1,2-Dichloroethane → HCID 86679520, compound

HRID 1776564Notes

Reaction equation

HRID 1776564 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=2[O:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:3][CH2:2]1.O[CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([O:12][CH2:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[O:11])=[CH:8][C:7]=2[O:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 86679519HCID 86679519, compound

Product 1

HCID 86679520HCID 86679520, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(cyclopropylmethoxy)-3-(methylsulfonyloxy)benzoic acid (0.300 g, 1.048 mmol), benzyl 2-hydroxyacetate (0.174 g, 1.048 mmol), EDC (0.603 g, 3.14 mmol), and DMAP (0.128 g, 1.048 mmol) in DCM (25 ml) was stirred at RT for 2 hours. The mixture was diluted with DCM and washed with HCl 1N and NaHCO35%. The organic phase was dried over Na2SO4, the solvent was removed under vacuum, and the crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 75:25). A further purification by trituration with EtOH was required to obtain 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-(methylsulfonyloxy)benzoate (0.238 g, 0.548 mmol, 52.3% yield, MS/ESI+ 434.9 [MH]+).

Workup

  1. washwashed with HCl 1N and NaHCO35%
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was removed under vacuum
  4. customthe crude was purified by flash chromatography on silica gel cartridge (petroleum ether:EtOAc=80:20 to 75:25)
  5. customA further purification by trituration with EtOH

Sources & evidence

ORD record
ord-265e3f1953da4d28ad4d99c96c4c4545
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…