Sodium borohydride → methyl (2E)-3-[4-(hydroxymethyl)thiophen-2-yl]prop-2-enoate

HRID 1465500Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[S:6][CH:7]=1)=[O:2].[BH4-].[Na+]>>[OH:2][CH2:1][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[S:6][CH:7]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 86650009methyl (2E)-3-(4-formylthiophen-2-yl)acrylate

Product 1

HCID 67030186methyl (2E)-3-[4-(hydroxymethyl)thiophen-2-yl]prop-2-enoateYield 92.6%

Procedure

By a method similar to Production Example 120, step 1, methyl (2E)-3-(4-formylthiophen-2-yl)prop-2-enoate (1.700 g, 8.664 mmol) was reduced with sodium borohydride to give methyl (2E)-3-[4-(hydroxymethyl)thiophen-2-yl]prop-2-enoate (1.591 g, yield 92.6%) as a white solid.

Sources & evidence

ORD record: ord-83414a59bf24466cbb4c927d550ae165
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999989B2

Reaction notes

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