Water → 4-Hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene

HRID 653444Notes

Reaction equation

HRID 653444 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[BH4-].[Na+].O>C(O)C>[OH:1][CH:2]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 4311764Sodium borohydride

Product 1

HCID 139116314-Hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 20 g (0.13 mol) of 4,5,6,7-tetrahydro-4-oxo-benzo[b]thiophene in 300 ml absolute ethanol was stirred with 5.4 g (0.14 mol) NaBH4 at ambient temperature for 20 hours. Then 200 ml H2O was added and the ethanol was removed under reduced pressure. The resulting mixture was extracted with ether. The combined organic extracts were backwashed with H2O, dried (Na2SO4), filtered, and evaporated under reduced pressure. The resultant colorless solid was triturated with hexane yielding 19.03 g (95%) of product, mp 58°-60° C.

Workup

  1. customthe ethanol was removed under reduced pressure
  2. extractionThe resulting mixture was extracted with ether
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customwas triturated with hexane yielding 19.03 g (95%) of product, mp 58°-60° C.

Sources & evidence

ORD record
ord-aa7ad1f832fe4e95a86b68ab47d57510
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

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