Carbonic acid, 1-chloroethyl ethyl ester → HCID 86628903, compound

HRID 1919429Notes

Reaction equation

HRID 1919429 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[C@@H:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:12]([OH:14])=[O:13])(=[O:7])=[O:6].[CH2:27]([O:29][C:30]([O:32][CH:33](Cl)[CH3:34])=[O:31])[CH3:28]>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[C@@H:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:12]([O:14][CH2:28][CH2:27][O:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:13])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 86628873HCID 86628873, compound

Product 1

HCID 86628903HCID 86628903, compound

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

Following the general procedure for the preparation of acyloxyalkyl/alkoxycarbonyloxyalkyl carboxylic esters from carboxylic acids of Description 22, (2R)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (11) (1.0 g, 2.4 mmol) dissolved in 15 mL of anhydrous toluene was reacted with 1.1 g (7.3 mmol) of commercially available 1-chloroethyl ethoxyformate in the presence of 0.81 g (2.9 mmol) of silver carbonate (Ag2CO3). After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:2) as eluent to provide 0.77 g of a mixture of the title compound (36a) and (3R)-4,4-dimethyl-3-[(4-methoxyphenyl)methoxy]-3,4,5-trihydrofuran-2-one. MS (ESI) m/z 546.99 (M+Na)+.

Workup

  1. customAfter work-up, the crude material was purified by silica gel column chromatography
  2. additiona mixture of ethyl acetate (EtOAc) and hexane (Hxn) (EtOAc/Hxn=1:2) as eluent

Sources & evidence

ORD record
ord-343a3a82d54d411ba0f92050b81ff314
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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