1,5-Dibromopentane → HCID 19996099, compound

HRID 2248393Notes

Reaction equation

HRID 2248393 reaction equation
[O: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]Br.[OH-].[Na+]>>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:8][CH2:7][CH2:6][C:5]1[O:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[CH:4]=1

Participants

4

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 11263674HCID 11263674, compound

Product 1

HCID 19996099HCID 19996099, compound

Procedure

A mixture of 2-benzo(b)furanethanol (2.00 g), 1,5-dibromopentane (6 ml), 50% sodium hydroxide (7 ml) and TAB (0.2 g) was vigorously stirred at 24° for 21 h, then partitioned between water (50 ml) and ether (60 ml). The organic phase was washed with brine (50 ml), dried and evaporated in vacuo. The oily residue was purified by FCC eluting with hexane-diethyl ether (97:3) to give the title compound as a colourless oil (2.70 g), t.l.c. (hexane-diethyl ether 4:1) Rf 0.54.

Workup

  1. custompartitioned between water (50 ml) and ether (60 ml)
  2. washThe organic phase was washed with brine (50 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customThe oily residue was purified by FCC
  6. washeluting with hexane-diethyl ether (97:3)

Sources & evidence

ORD record
ord-1604bac49a6f499e8ca4360801d75ead
Source dataset
uspto-grants-1991_08
Patent number
US05039697

Reaction notes

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