Diiodomethane → HCID 21185954, compound

HRID 1384176Notes

Reaction equation

HRID 1384176 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:20]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:23][CH:24]=3)=[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:20]=[C:21]([CH:22]=[CH:23][CH:24]=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 21185885HCID 21185885, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 21185954HCID 21185954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diiodomethane (1.1 ml, 13.7 mmol) is added dropwise, at 60° C., to a mixture of methyl 3-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)vinyl]phenylcarboxylate (2.2 g, 6.3 mmol) and a 1M solution of diethylzinc in heptane (13 ml, 13 mmol) in dichloromethane (50 ml). The heating is continued for 15 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 sulphate and concentrated.

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 sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b57dd1c2a050456992943a968d1332a1
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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