3,4-dihydro-2H-pyran → Cyclohexanecarboxylic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, ethyl ester

HRID 84228ノート

反応式

HRID 84228 の反応式
[NH+]1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[OH:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.[O:30]1[CH:35]=[CH:34][CH2:33][CH2:32][CH2:31]1>C(Cl)Cl>[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:18][CH:19]1[CH2:20][CH2:21][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:23][CH2:24]1

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

生成物 1

HCID 67249083Cyclohexanecarboxylic acid, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-, ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Pyridinium-4-toluenesulfonate (2.57 g, 10.2 mmol) was added to a solution of ethyl 4-hydroxycyclohexanecarboxylate (8.8 g, 51.10 mmol) and 3,4-dihydro-2H-pyran (8.60 g, 102 mmol) in DCM (200 mL). After 16 hours the reaction was quenched with saturated aqueous sodium bicarbonate. The layers were separated and the organic layer was washed with water. The organic layer was dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography on an Analogix SF65-200g column (hexanes/ethyl acetate 95:05-9:1) afforded the title compound (clear oil) as a mixture of isomers (11.1 g, 85%).

後処理

  1. customAfter 16 hours the reaction was quenched with saturated aqueous sodium bicarbonate
  2. customThe layers were separated
  3. washthe organic layer was washed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on an Analogix SF65-200g column (hexanes/ethyl acetate 95:05-9:1)

出典と根拠

ORDレコード
ord-2eee8da468864ba09094f09582de6ed2
出典データセット
uspto-grants-2014_09
特許番号
US08846933B2

反応ノート

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