Diethyl Ether → HCID 19996076, compound

HRID 359750Notes

Reaction equation

HRID 359750 reaction equation
[S:1]1[C:5]([CH2:6][CH2:7][OH:8])=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+].CCOCC>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:8][CH2:7][CH2:6][C:5]1[S:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 280609Benzo(b)thiophene-2-ethanol

Product 1

HCID 19996076HCID 19996076, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Benzo[b]thiopheneethanol (2.20 g), 1,6-dibromohexane (2.59 ml), TAB (0.25 g), aqueous 12.5M sodium hydroxide (9 ml), and ether (20 ml) were stirred overnight at room temperature. The mixture was diluted with water (50 ml), extracted with ether (3×50 ml), and the combined, dried extracts were evaporated. The residual oil was purified by FCC eluting with cyclohexane-diethyl ether (100:0→98:2) to give the title compound as a colourless oil (2.73 g).

Workup

  1. extractionextracted with ether (3×50 ml)
  2. customdried extracts
  3. customwere evaporated
  4. customThe residual oil was purified by FCC
  5. washeluting with cyclohexane-diethyl ether (100:0→98:2)

Sources & evidence

ORD record
ord-6f0b0231964d458cb14d3f00e3aa7543
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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