Methanol → HCID 66699549、化合物

HRID 1161028

反応式

HRID 1161028 の反応式
[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([O:25]C3CCCCO3)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[OH:37])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO.ClCCl>C(OCC)(=O)C>[C:1]([C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]([OH:25])[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:14][CH:15]=2)=[C:6]([CH2:34][CH2:35][CH3:36])[C:5]=1[OH:37])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 887MethanolHCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 666996043-[[4-(4-Acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

生成物 1

HCID 66699549HCID 66699549、化合物収率 93%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Stir a mixture of 3-[[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (13.4 g, 26.88 mmol), p-toluenesulfonic acid monohydrate (5.1 g, 26.88 mmol), methanol (100 mL), dichloromethane (50 mL), and ethyl acetate (50 mL) at room temperature for an hour. Concentrate the reaction mixture, dilute with ethyl acetate (150 mL) and wash with water (2×100 mL). Dry the organic phase over magnesium sulfate, filter, and concentrate. Dilute the residue with 5:1 hexanes:dichloromethane (50 mL), cool to 0° C. and filter. Collect a second and third crop to give the title compound (10.3 g, 93%), as a white solid. LCMS 416 M+1.

後処理

  1. concentrationConcentrate the reaction mixture
  2. additiondilute with ethyl acetate (150 mL)
  3. washwash with water (2×100 mL)
  4. dry with materialDry the organic phase over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. additionDilute the residue with 5:1 hexanes
  8. filtrationfilter
  9. customCollect a second and third crop

出典と根拠

ORDレコード
ord-faddbb6ac0d644f8850447eac37b3f1d
出典データセット
uspto-grants-2010_10
特許番号
US07816523B2

関連ノート

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