1,2-Dichloroethane → 2-(Benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate

HRID 1776572Notes

Reaction equation

HRID 1776572 reaction equation
C(Cl)CCl.[OH:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH:17]1([CH2:20][O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=2[CH:31]=[O:32])[CH2:19][CH2:18]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:17]1([CH2:20][O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([O:5][CH2:6][C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])=[O:27])=[CH:24][C:23]=2[CH:31]=[O:32])[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 561337Benzyl 2-hydroxyacetateHCID 866795274-(Cyclopropylmethoxy)-3-formylbenzoic acid

Product 1

HCID 866795282-(Benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

EDC (2.52 g, 13.16 mmol) was added to a solution of compound benzyl 2-hydroxyacetate (2.02 g, 12.15 mmol), 4-(cyclopropylmethoxy)-3-formylbenzoic acid (2.23 g, 10.13 mmol), and DMAP (247 mg, 2.03 mmol) in DCM (20 ml) at RT under nitrogen atmosphere. The mixture was stirred at RT overnight. The mixture was then diluted with DCM and washed with NaHCO3 sat. sol., HCl 0.1M and brine. The organic phase was dried over Na2SO4, and the solvent was evaporated. 2-(benzyloxy)-2-oxoethyl 4-(cyclopropylmethoxy)-3-formylbenzoate was obtained (3.73 g, quantitative yield).

Workup

  1. washwashed with NaHCO3 sat. sol., HCl 0.1M and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-70afe14a30e54ea3be47260b4c2dba55
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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