HCID 18548200, compound → HCID 18548215, compound

HRID 840066Notes

Reaction equation

HRID 840066 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 90%

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 (90% purity).

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-7e376be54a794dbca9bb6a839d227aeb
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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