Diiodomethane → HCID 23144974, compound

HRID 1867227Notes

Reaction equation

HRID 1867227 reaction equation
[CH2:1](I)I.[CH3:4][C:5]([CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:6][CH2:7][CH3:8]>C(OC)(C)(C)C>[CH2:7]([CH:6]1[CH2:4][C:5]1([CH3:1])[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[OH:15])[CH3:8]

Participants

4

Reactant 2

HCID 6346DiiodomethaneHCID 1633364-Methyl-3-decen-5-ol2×

Product 1

HCID 23144974HCID 23144974, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a dry 2 liter multi-neck round bottom flask fitted with an air stirrer, nitrogen inlet condenser and an addition funnel 8 g of a ZnCu and 75 ml of Methyl Tertiary Butyl Ether (MTBE) was added. The resulting mixture was stirred for 5 minutes. After the temperature of the mixture was stabilized, 24 g of CH2I2 was added over 10 minutes while stirring. After the temperature of the mixture was stabilized, the mixture was heated to reflux. As the temperature of the mixture reached 44° C., 17 g of 4-methyl-3-decene-5-ol was added over 30 minutes. After the addition of 4-methyl-3-decene-5-ol, a first sample was taken. Additional samples were taken every hour for three hours. Then the sample was quenched with saturated NH4Cl, aqueous layer separated and the organic layer filtered through celite.

Workup

  1. additionwas added
  2. stirringwhile stirring
  3. temperaturethe mixture was heated to reflux
  4. customreached 44° C.
  5. waitAdditional samples were taken every hour for three hours
  6. customThen the sample was quenched with saturated NH4Cl, aqueous layer
  7. customseparated
  8. filtrationthe organic layer filtered through celite

Sources & evidence

ORD record
ord-6e900f5c6f9c4854ac9ed1ebb8cde1a5
Source dataset
uspto-grants-2009_12
Patent number
US07632800B2

Reaction notes

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