Trichloroacetyl chloride → 6,6-Dichloro-2-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.2.0]heptan-7-one

HRID 569228Notes

Reaction equation

HRID 569228 reaction equation
[CH3:1][C:2]([Si:5]([CH3:18])([CH3:17])[O:6][CH:7]([CH2:15][CH3:16])[CH2:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]=[CH:11]1)([CH3:4])[CH3:3].[Cl:19][C:20](Cl)([Cl:24])[C:21](Cl)=[O:22].P(Cl)(Cl)(Cl)=O>CCOCC.[Zn].[Cu]>[Cl:19][C:20]1([Cl:24])[CH:12]2[CH:11]([CH:10]([CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:2]([CH3:3])([CH3:1])[CH3:4])([CH3:17])[CH3:18])[CH2:15][CH3:16])[CH2:14][CH2:13]2)[C:21]1=[O:22]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 139240763-(3-[(1,1-Dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene

Product 1

HCID 142041096,6-Dichloro-2-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.2.0]heptan-7-oneYield 62.5%

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In the next step, the procedure of Example 6C is used, but there are substituted: 3-(3-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)cyclopentene ([3-(2-cyclopenten-1-yl)-1-ethylpropoxy](1,1-dimethylethyl)dimethylsilane) (15 g, 0.056 moles) dissolved in ether (100 ml), trichloroacetyl chloride (20.3 g, 0.11 moles) and phosphorous oxychloride (17.2 g, 0.11 moles) both dissolved in ether (50 ml), zinc/copper couple (10 g, 0.16 moles). The crude product is subjected to short path vacuum distillation leaving a clear yellow oil (13.5 g, 0.035 moles) of 7,7-dichloro-4-[3-[[1,1-dimethylethyl)dimethylsilyloxy]pentyl]bicyclo[3.2.0]heptan-6-one.

Workup

  1. distillationThe crude product is subjected to short path vacuum distillation

Sources & evidence

ORD record
ord-2d9810a08e494147bf9760d7dd220703
Source dataset
uspto-grants-1988_03
Patent number
US04731458

Reaction notes

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