Acetyl chloride → HCID 58516442, compound

HRID 43320Notes

Reaction equation

HRID 43320 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:22](=[O:23])[CH2:21][CH:20]([CH:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[CH2:19][C:18]1=[O:29].[C:30](Cl)(=[O:32])[CH3:31]>ClCCl>[C:30]([O:23][C:22]1[CH2:21][CH:20]([CH:24]2[CH2:28][CH2:27][O:26][CH2:25]2)[CH2:19][C:18](=[O:29])[C:17]=1[C:10]1[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67177746HCID 67177746, compound

Product 1

HCID 58516442HCID 58516442, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (0.11 ml, 0.79 mmol) in dichloromethane (2 ml) is added dropwise to a chilled (ice-bath) solution of 2-(2,4,6-trimethylphenyl)-5-(tetrahydrofuran-3-yl)cyclohexane-1,3-dione (prepared by a method analogous to that described in Example 2) and acetyl chloride (0.056 ml, 0.79 mmol) in dichloromethane (4.5 ml). Once the addition is complete the cooling bath is removed and the reaction mixture is stirred at room temperature overnight. The reaction mixture is diluted with dichloromethane (35 ml) and washed with saturated aqueous sodium bicarbonate solution (20 ml). The organic phase is dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 3-oxo-5-(tetrahydrofuran-3-yl)-2-(2,4,6-trimethylphenyl)cyclohex-1-enyl acetate.

Workup

  1. customprepared by a method analogous to
  2. additionOnce the addition
  3. customis removed
  4. additionThe reaction mixture is diluted with dichloromethane (35 ml)
  5. washwashed with saturated aqueous sodium bicarbonate solution (20 ml)
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe filtrate is evaporated in vacuo
  9. customThe residue is purified by column chromatography on silica gel
  10. washeluting with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-5bc635600cce44a49002132a304b5b70
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Reaction notes

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