1,2-Dichloroethane → HCID 178527035, compound

HRID 902939Notes

Reaction equation

HRID 902939 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][PH:11](=[O:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:14]([O:13][PH:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 178527055HCID 178527055, compound

Product 1

HCID 178527035HCID 178527035, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of example 80 (1.75 g, 8.83 mmol) in dry CH2Cl2 (40 mL) was added benzyl alcohol (1.83 mL, 17.7 mmol), DMAP (108 mg, 0.88 mmol) and EDC (1.91 g, 10.0 mmol). The mixture was then stirred at room temperature for 18 h. The mixture was concentrated in vacuum, taken-up in ethyl acetate and washed with NaHCO3 (5%) and H2O. Drying (Na2SO4) and concentration gave 2.8 g of a pale yellow oil which was purified by flash chromatography (SiO2, ethyl acetate:hexane (1:1)) to give 1.92 g of the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuum, taken-up in ethyl acetate
  2. washwashed with NaHCO3 (5%) and H2O
  3. customDrying
  4. concentration(Na2SO4) and concentration

Sources & evidence

ORD record
ord-12f7746b5f2840b2b3bcc7c4190e76de
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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