Sodium borohydride → 2-Hydroxymethyl-3,4,5-trimethyl-thiophene

HRID 904444Notes

Reaction equation

HRID 904444 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([CH3:8])[S:4][C:3]=1[CH:9]=[O:10].[BH4-].[Na+]>C(O)C>[OH:10][CH2:9][C:3]1[S:4][C:5]([CH3:8])=[C:6]([CH3:7])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 128752623,4,5-Trimethylthiophene-2-carbaldehyde

Product 1

HCID 128752592-Hydroxymethyl-3,4,5-trimethyl-thiophene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.9 G. of 3,4,5-trimethyl-2-thiophenecarboxaldehyde were dissolved in 20 ml. of ethanol. The resulting solution was cooled to 0°-5° C. and 125 mg. of sodium borohydride were added in small portions. The resulting reaction mixture was stirred at room temperature for 3 hours, poured into ice water, extracted with ethyl acetic, dried with sodium sulfate, filtered and evaporated. The resulting crystalline 2-hydroxymethyl-3,4,5-trimethyl-thiophene had m.p. 45°-48° C.

Workup

  1. temperatureThe resulting solution was cooled to 0°-5° C.
  2. customThe resulting reaction mixture
  3. extractionextracted with ethyl acetic
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d3d32c7ac19a4d64a645660e1f663aa1
Source dataset
uspto-grants-1980_10
Patent number
US04230872

Reaction notes

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