Water → HCID 131717856, compound

HRID 1590402Notes

Reaction equation

HRID 1590402 reaction equation
CC(NC(=O)/C=C/C=[CH:11]/[C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[C:22](Br)Br)=[CH:17][CH:16]=1)C(C)C.C([Li])CCC.[OH2:31]>O1CCCC1>[C:21]([C:18]1[CH:19]=[CH:20][C:15]([C@@H:13]2[CH2:14][C@H:12]2[CH2:11][OH:31])=[CH:16][CH:17]=1)#[CH:22]

Participants

5

Reactant 3

HCID 962WaterHCID 131717857HCID 131717857, compoundHCID 178418339Butyllithium

Product 1

HCID 131717856HCID 131717856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-Trans-2-[4-(2,2-dibromoethenyl)phenyl]cyclopropylmethanol (1.43 g) (prepared as in example 16) in dry tetrahydrofuran under nitrogen at -40° was treated with n-butyllithium (8.1 ml) After 4 hours at 25° water was added and the mixture worked up in the usual manner. Purification by chromatography (silica ether/hexane) gave (±)-trans-2-(4-ethynylphenyl)cyclopropane methanol (0.62 g). NMR 1H: 7.41(2H,d), 6.90(2H,d), 3.30(2H,d), 2.95(1H,s), 2.59(1H,s), 1.85(1H,m), 1.34(1H,m), 0.90(2H,m).

Workup

  1. additionwas added
  2. customPurification by chromatography (silica ether/hexane)

Sources & evidence

ORD record
ord-cb080d643a874f2db63d1bd59f9804c3
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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