Dimethylformamide → 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester

HRID 1807045ノート

反応式

HRID 1807045 の反応式
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:8]1(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([CH3:7])[CH3:6])[CH3:2].S(Cl)(Cl)=O.CN(C)C=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]=1)([CH3:7])[CH3:6])[CH3:2]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 62399213Ethyl tetrahydro-4-hydroxy-alpha,alpha-dimethyl-2H-pyran-4-acetate

生成物 1

HCID 672969602-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester収率 99%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

Step B To a solution of 2-(4-hydroxy-tetrahydro-pyran-4-yl)-2-methyl-propionic acid ethyl ester (19.5 g, 90 mmol) in chloroform (100 mL) was added thionyl chloride (13.3 mL, 180 mmol) and dimethylformamide (0.28 mL). The reaction mixture was heated at 100° C. for 18 h, then cooled to room temperature and concentrated. To the resulting residue was added aqueous NaOH solution (10 N) to adjust the “pH” of the mixture to basic. The mixture was then extracted with ethyl acetate twice. The combined organic extracts were washed with water, brine, dried over MgSO4, and concentrated to give 2-(3,6-dihydro-2H-pyran-4-yl)-2-methyl-propionic acid ethyl ester as a brown oil (17.6 g, 99%).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. additionTo the resulting residue was added aqueous NaOH solution (10 N)
  4. extractionThe mixture was then extracted with ethyl acetate twice
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-9df3eba99a684c4dbeab313e340eaa4d
出典データセット
uspto-grants-2013_01
特許番号
US08354444B2

反応ノート

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