HCID 22621649, compound → HCID 22621680, compound

HRID 840075Notes

Reaction equation

HRID 840075 reaction equation
Br[C:2]1(Br)[CH2:4][C:3]1(Br)[CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[Li]>CCOCC>[CH2:7]([O:6][CH2:5][C:3]1[CH2:4][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 22621649HCID 22621649, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22621680HCID 22621680, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1.15 g of 1,1,2-tribromo-2-(hexyloxymethyl)cyclopropane (2.9 mmol) in 6 ml of ether was treated at −78° C. with 1.4 ml of methyllithium (1.4 M, 8.8 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 320 mg of 1-hexyloxymethyl-cyclopropene, as a dark yellow liquid.

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-9b7870e4cda740bca1fcca2cc22e50ed
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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