[oeunaa]

I need help with how this reaction will precede as well as what intermediates and products are formed.
1. 0.400 g of Compound A is dissolved in 5 mL of methanol and cooled to 0 °C.
2. Sodium borohydride (0.145 g) was added slowly, and the reaction progress was monitored by TLC.
3. Based on the TLC is the reaction done?

I have attached an image of my work so far as well as the TLC plate.
I know the TLC plate shows the reaction is not complete. The product of the reaction should be less polar than compound A. I have never seen a TLC plate with the lower dots not on the SM, CS, RM line. i have also attached a picture of how the TLCs ive normally encountered look like.

[Hunter2]

Methanol is only solvent. Boronhydride reduced aldehydes and ketons.

[rolnor]

you wright methoxy, check borohydride reduction on wiki  your product will be on baseline in your TLC-system, very polar  EtOAc9MeOH1 will make it move on TLC

[Babcock_Hall]

The formula you provided for sodium borohydride is not correct, and that is not the only error.

[rolnor]

Yes, I see now, its confusing. But just check sodium borohydride on wikipedia will clear things