Methyl chloroformate → HCID 67604256, compound

HRID 1450119Notes

Reaction equation

HRID 1450119 reaction equation
C=CCCC.C([Li])(C)(C)C.[CH3:11][CH:12]([CH:16]([CH3:18])[CH3:17])/[CH:13]=[CH:14]/I.[C:19]([CH:22]1[C:30]2([CH3:31])[CH:25]([C:26](=[CH:32][CH:33]([C:36]34[CH2:41][CH:40]3[CH2:39][CH:38]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:37]4=[CH2:50])[O:34][CH3:35])[CH2:27][CH2:28][CH2:29]2)[CH2:24][CH2:23]1)(=[O:21])[CH3:20].Cl[C:52]([O:54][CH3:55])=[O:53].C(=O)([O-])O.[Na+]>C(OCC)C.O1CCCC1>[CH3:11][CH:12]([CH:16]([CH3:18])[CH3:17])/[CH:13]=[CH:14]/[C@@:19]([CH:22]1[C:30]2([CH3:31])[CH:25]([C:26](=[CH:32][CH:33]([C:36]34[CH2:41][CH:40]3[CH2:39][CH:38]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:44])[CH3:45])[C:37]4=[CH2:50])[O:34][CH3:35])[CH2:27][CH2:28][CH2:29]2)[CH2:24][CH2:23]1)([O:21][C:52]([O:54][CH3:55])=[O:53])[CH3:20]

Participants

9

Reactant 6

HCID 6586Methyl chloroformateHCID 80041-PenteneHCID 516892Sodium BicarbonateHCID 23353003HCID 23353003, compoundHCID 57004801HCID 57004801, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67604256HCID 67604256, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.3 ml of 1.5M pentene solution of t-butyllithum was dropwise added, at -78° C., to a solution 416 mg of (E)-3,4-dimethyl-1-iodo-1-pentene dissolved in 5 ml of diethyl ether. The reaction mixture was stirred at room temperature for 2 hours. Thereto was dropwise added a solution of 682 mg of 1-acetyl-4-(2-(3-(t-butyldimethylsilyloxy)-2-methylenebicyclo[3.1.0]hexane-1-yl)-2-methoxyethylidene)-2,3,3a,4,5,6,7,7a-octahydro-7a-methylindene dissolved in 10 ml of tetrahydrofuran. The mixture was stirred for 1 hour. Thereto was dropwise added 0.3 ml of methyl chloroformate. The mixture was stirred at room temperature overnight. The reaction mixture was mixed with an aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and concentrated under reduced pressure to obtain 1.04 g (2S,3E)-5,6-dimethyl-2-(4-(2-(3-(t-butyldimethylsilyloxy)-2-methylenebicyclo[3.1.0]hexane-1-yl)-2-methoxyethylidene)-2,3,3a,4,5,6,7,7a-octahydro-7a-methylinden-1-yl)-2-methoxycarbonyloxy-3-heptene having the follow property.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with an aqueous sodium hydrogencarbonate solution
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e847433fb26b46449d63393d64d8876a
Source dataset
uspto-grants-1997_02
Patent number
US05600047

Reaction notes

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