Diiodomethane → HCID 21185969, compound

HRID 1384175Notes

Reaction equation

HRID 1384175 reaction equation
ICI.[CH3:4][C:5]1([CH3:29])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]2[CH:10]=[C:9]([C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([O:27][CH3:28])=[O:26])=[CH2:18])[CH:8]=[CH:7][C:6]1=2.[CH2:30]([Zn]CC)C.CCCCCCC>ClCCl>[CH3:4][C:5]1([CH3:29])[CH2:14][CH2:13][C:12]([CH3:15])([CH3:16])[C:11]2[CH:10]=[C:9]([C:17]3([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([O:27][CH3:28])=[O:26])[CH2:30][CH2:18]3)[CH:8]=[CH:7][C:6]1=2

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 8900HeptaneHCID 21185896HCID 21185896, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 21185969HCID 21185969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diiodomethane (230 μl, 2.85 mmol) is added dropwise, at 60° C., to a mixture of methyl 2-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate (500 mg, 1.44 mmol) and a 1M solution of diethylzinc in heptane (2.9 ml, 2.9 mmol) in dichloromethane (10 ml). The heating is continued for 4 h. The solution is extracted with ethyl acetate. After separation of the phases by settling, the organic phase is washed with 1N HCl solution and then with water, dried over anhydrous magnesium sulfate and concentrated. The same process is repeated once.

Workup

  1. extractionThe solution is extracted with ethyl acetate
  2. customAfter separation of the phases
  3. washthe organic phase is washed with 1N HCl solution
  4. dry with materialwith water, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-679ddd18c29b4ad1aefb12cdd8c39923
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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