Bromide ion → 1-Bromo-5,5-dimethyl-3-tetrahydropyranyloxy-trans-1-octene

HRID 1903992Notes

Reaction equation

HRID 1903992 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:14][CH2:15][CH3:16])[CH2:3][CH:4]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)[C:5]#[CH:6].C(BC(C(C)C)C)(C(C)C)C.[Br-:29]>C(Cl)(Cl)(Cl)Cl>[Br:29]/[CH:6]=[CH:5]/[CH:4]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)[CH2:3][C:2]([CH3:17])([CH3:1])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 259Bromide ionHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 538897305,5-Dimethyl-3-tetrahydropyranyloxy-1-octyne

Product 1

HCID 867329731-Bromo-5,5-dimethyl-3-tetrahydropyranyloxy-trans-1-octene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Treatment of 7.15 g. (30 moles) of 5,5-dimethyl-3-tetrahydropyranyloxy-1-octyne (Example 999) with 33 moles of disiamylborane in carbon tetrachloride followed by 30 moles of bromide in carbon tetrachloride, refluxing the resulting mixture, and isolation by chromatography on silica gel, all as described in Example 1173 gives the title compound.

Workup

  1. temperaturerefluxing the resulting mixture, and isolation by chromatography on silica gel

Sources & evidence

ORD record
ord-78dc56d53c604d269b49f4da13e8178e
Source dataset
uspto-grants-1984_03
Patent number
US04439365

Reaction notes

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