Trichloroacetyl chloride → HCID 57098043, compound

HRID 652986Notes

Reaction equation

HRID 652986 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:31](Cl)(Cl)[C:32](Cl)=[O:33].P(Cl)(Cl)(Cl)=O>[Cu].[Zn].C(OCC)C>[CH2:1]([O:8][CH2:9][C:10]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][C:32](=[O:33])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 20196448HCID 20196448, compound

Product 1

HCID 57098043HCID 57098043, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture containing 7.18 g (18 mmol) of the compound prepared in (a) above, 75 ml of anhydrous diethyl ether and 1.4 g of zinc-copper couple was blanketed with nitrogen and treated dropwise at room temperature with a solution containing 3.63 g (20 mmol) of trichloroacetyl chloride and 3.06 g (20 mmol) of phosphorus oxychloride. After stirring the mixture at room temperature for 48 hours, the salts were filtered off and the filtrate concentrated in vacuo. The residue was then chromatographed on silica gel employing a mixture of petroleum ether and methyl-t-butyl ether in a ratio of 9:1 as the eluent to yield a yellow oil.

Workup

  1. additiontreated dropwise at room temperature with a solution
  2. filtrationthe salts were filtered off
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was then chromatographed on silica gel employing
  5. additiona mixture of petroleum ether and methyl-t-butyl ether in a ratio of 9:1 as the eluent
  6. customto yield a yellow oil

Sources & evidence

ORD record
ord-fa953e530a6b4e9fa8d35264a3965288
Source dataset
uspto-grants-1987_06
Patent number
US04673672

Reaction notes

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