Chloroform → HCID 13896199, compound

HRID 1199691Notes

Reaction equation

HRID 1199691 reaction equation
C(Cl)(=O)C.[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH2:13][CH2:14][C@@H:15]1[O:20][C:19](=[O:21])[CH2:18][C@@H:17](O)[CH2:16]1.C(Cl)(Cl)Cl.C(N(CC)CC)C>O.C(OCC)C>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[CH2:13][CH2:14][CH:15]1[O:20][C:19](=[O:21])[CH:18]=[CH:17][CH2:16]1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67708270HCID 67708270, compound

Product 1

HCID 13896199HCID 13896199, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Acetyl chloride (8.6 ml) was added slowly to a vigorously stirred solution of trans-6-[2-(2,4-dichlorophenyl)ethyl]-3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-one (19.3 g, 66.8 mmol), CHCl3 (200 ml), triethylamine (35 ml) and 4-(dimethylasmino)pyridine (100 mg) at 20° C. The cloudy Pale amber mixture was stirred at ambient temperature for 16 hours and then distributed between diethyl ether (300 ml) and H2O (300 ml). The organic layer was separated and washed with IN HCl 200 ml) and H2O (2×200 ml), then dried and evaporated. The pale amber residual oil slowly solidified. Crystallization from n-butyl chloride:hexane; 1:5(v:V) provided the title compound as small pale amber needles. m.p. 69°-70° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with IN HCl 200 ml) and H2O (2×200 ml)
  3. customdried
  4. customevaporated
  5. customCrystallization from n-butyl chloride

Sources & evidence

ORD record
ord-cc1fd8281e4e496593120b4223e6fb49
Source dataset
uspto-grants-1990_02
Patent number
US04902709

Reaction notes

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