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

HRID 632557

反応式

HRID 632557 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf0b6851f62540ed90d2178487d58f20
出典データセット
uspto-grants-2016_04
特許番号
US09321753B2

関連ノート

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