Diethyl Ether → HCID 19996076, compound

HRID 1086904Notes

Reaction equation

HRID 1086904 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). Analysis Found: C, 56.55; H, 6.3; Br, 23.8; S, 9.4. C16H21BrOS requires C, 56.3; H, 6.2; Br, 23.4; S, 9.4%.

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-fcb5ef77844749f5b67359ad8d3cb025
Source dataset
uspto-grants-1991_07
Patent number
US05032609

Reaction notes

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