Hydrochloric Acid → Acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester

HRID 1894848

반응식

HRID 1894848 반응식
[OH:1][C@H:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][O:4][C:3]1=[O:9].C(N(C(C)C)CC)(C)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21].Cl>ClCCl.CCOC(C)=O>[CH3:7][C:6]1([CH3:8])[CH2:5][O:4][C:3](=[O:9])[CH:2]1[O:1][C:19](=[O:22])[CH:20]=[CH2:21]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 736053(+)-Pantolactone

생성물 1

HCID 3529221Acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester수율 57%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) was prepared in the following manner: 3-(S)-Hydroxy-4,4-dimethyl-dihydro-furan-2-one (2.60 g, 20 mmol) and diisopropylethylamine (5.2 mL, 30 mmol) in dichloromethane (25 mL) was cooled to −10° C. and treated dropwise with acryloyl chloride (2.03 mL, 25 mmol) and stirred for 2 h. 1M HCl (20 mL) was added and the organic layer was washed with sodium bicarbonate and water. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography (10-40% EtOAc, hexanes) afforded 2.09 g (57% yield) of the desired acrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) as a clear oil. This substrate was used to prepare the acid chloride of (1R)-4-methyl-cyclohex-3-enecarboxylic acid analogous to the procedure described in Scheme 15 and Scheme 16.

후처리

  1. customAcrylic acid 4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester (R) was prepared in the following manner
  2. washthe organic layer was washed with sodium bicarbonate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d1c46801d9a049babb27b3a99eb86b82
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513298B2

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