1,5-Dibromopentane → HCID 19996099, compound

HRID 359743Notes

Reaction equation

HRID 359743 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-a1b311aff7794e83ad475e2cf1275110
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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