Benzo[b]thiophene-3-acetic acid → 2-(Benzo[b]thiophen-3-yl)ethanol

HRID 1023889Notes

Reaction equation

HRID 1023889 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11](O)=[O:12])=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[S:1]1[CH:2]=[C:3]([CH2:10][CH2:11][OH:12])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

4

Reactant 2

HCID 70799Benzo[b]thiophene-3-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 158522062-(Benzo[b]thiophen-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-benzothienylacetic acid (5.2 mmol) in 10 mL of anhydrous THF was slowly added to a stirred solution of LAH (10.4 mmol) in 50 mL of THF at 0° C. The ice bath was removed and the solution was stirred overnight, while it was allowed to warm to room temperature. The reaction was quenched by addition of water, 10% aqueous NaOH. The mixture was filtered over Celite and the filtrate was concentrated to give 2-(benzo[b]thiophen-3-yl)ethanol, which was used for tosylation.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched by addition of water, 10% aqueous NaOH
  3. filtrationThe mixture was filtered over Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-55052d06de4a44c0b786fff16ac1eb7f
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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