Sodium borohydride → 1-(5-Hydroxymethylthiophen-2-yl)-cyclopent-3ene carboxylic acid ethyl ester

HRID 481389Notes

Reaction equation

HRID 481389 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=2)[CH2:7][CH:8]=[CH:9][CH2:10]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 542933021-(5-Formylthiophen-2-yl)cyclopent-3ene carboxylic acid ethyl ester2×

Product 1

HCID 570398381-(5-Hydroxymethylthiophen-2-yl)-cyclopent-3ene carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step 2, above (3) (0.93 mmol), in 3 ml methanol at 0° C. was added sodium borohydride (2.0 mmol). The reaction was slowly allowed to warm to ambient temperature and was stirred for 2 hours. The reaction was quenched with saturated ammonium chloride and extracted (2×10 ml EtOAc). The organic extracts were combined and washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated to yield the title compound (4).

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted (2×10 ml EtOAc)
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b4742ebe42bf48398b671ad41c520642
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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