Ethanol → HCID 131729098, compound

HRID 1671424Notes

Reaction equation

HRID 1671424 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[CH: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].[C:27](Cl)(=O)[C:28](Cl)=O.C(O)C.N1C=CC=CC=1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[CH: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][CH2:27][CH3:28])=[O:13])(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 87601326HCID 87601326, compound

Product 1

HCID 131729098HCID 131729098, compoundYield 506.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (14) (0.5 g, 1.2 mmol) dissolved in 5 mL of anhydrous dichloromethane (DCM) was reacted with 0.14 mL (0.2 g, 0.14 mmol) of oxalyl chloride. After the reaction was complete, a solution of 5 mL of ethanol (EtOH) and 0.16 mL of pyridine (0.15 g, 1.9 mmol) was added to the acid chloride. 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 0.31 g (58% yield) of the title compound (23a) as a colorless oil. Rf=0.59 (EtOAc/Hxn=1:2). 1H NMR (400 MHz, CDCl3): δ=1.05 (s, 3H), 1.06 (s, 3H), 1.33 (t, J=6.8 Hz, 3H), 2.25-2.33 (m, 2H), 3.22-3.26 (m, 2H), 3.65-3.68 (m, 2H), 3.81 (s, 1H), 3.82 (s, 3H), 3.97 (d, J=9.2 Hz, 1H), 4.19-4.31 (m, 4H), 4.56 (d, J=11.2 Hz, 1H), 6.88 (d, J=8.4 Hz, 2H), 7.26 (d, J=9.2 Hz, 2H) ppm. MS (ESI) m/z 458.97 (M+Na)+. The analytical data was consistent with the proposed structure.

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-53ac42912ae04186ac119f8c37f7c579
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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