Methanol → HCID 66699549, 화합물

HRID 1161028

반응식

HRID 1161028 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 66699549HCID 66699549, 화합물수율 93%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-faddbb6ac0d644f8850447eac37b3f1d
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816523B2

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