HCID 18548200, compound → HCID 18548215, compound

HRID 1265990Notes

Reaction equation

HRID 1265990 reaction equation
Br[C:2]1(Br)[CH2:4][C:3]1(Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].C[Li]>CCOCC>[OH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]1[CH2:4][CH:2]=1

Participants

4

Reactant 2

HCID 18548200HCID 18548200, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 18548215HCID 18548215, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.0 g 1,1,2-tribromo-2-(7-hydroxyheptyl)cyclopropane (2.5 mmol) in 25 ml of ether was treated at −78° C. with 7.2 ml of methyllithium (1.4 M, 10 mmol). After 5 minutes, the reaction mixture was warmed to 0° C. and held at this temperature. The reaction was quenched with saturated ammonium chloride. The reaction mixture was washed with water and brine, dried over magnesium sulfate, filtered and stripped to give 240 mg of 1-(7-hydroxyheptyl)-cyclopropene.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3ec421d1bfcf4aa496964304b9ab044c
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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