Acetic Acid → (5-(2-Cyclopropylvinyl)thiophen-2-yl)methanol

HRID 2080139Notes

Reaction equation

HRID 2080139 reaction equation
[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].C(O)(=O)C.O>O1CCCC1CCO>[CH:1]1([CH:4]=[CH:5][C:6]2[S:10][C:9]([CH2:11][OH:12])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 740199705-(2-Cyclopropylvinyl)thiophen-2-aldehyde

Product 1

HCID 67119677(5-(2-Cyclopropylvinyl)thiophen-2-yl)methanolYield 96.2%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

5-(2-Cyclopropylvinyl)thiophen-2-aldehyde described in Preparation Example 148 (960 mg, 5.39 mmol) was dissolved in a mixture solvent of tetrahydrofuran-ethanol (2:1) (30 mL), sodium borohydride (100 mg, 2.64 mmol) was added under stirring on an ice bath, and the solution was stirred for 30 minutes. Acetic acid (0.5 mL) and water (10 mL) were added sequentially to the reaction solution, which was then extracted with ethyl acetate (50 mL). The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, and the title compound (930 mg, 5.19 mmol, 96.2%) was obtained as a colorless oil.

Workup

  1. additionwas added
  2. stirringthe solution was stirred for 30 minutes
  3. extractionwas then extracted with ethyl acetate (50 mL)
  4. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-213e0479cb9546c9b74c1019441d7de4
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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