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Water → HCID 66699467, 화합물

HRID 1717721
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HRID 1717721 반응식
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([SH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].I[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(=O)CC>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([S:11][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C@H:23]([O:32][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][O:34]3)[C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[C:27]#[N:28])=[CH:21][CH:22]=2)=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 132955181-(2-Hydroxy-3-propyl-4-sulfanylphenyl)ethan-1-oneHCID 57884505(S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile

생성물 1

HCID 66699467HCID 66699467, 화합물수율 53.4%

시약·촉매·용매 1

HCID 6569
Methyl Ethyl Ketone
용매

실험 절차

Stir a mixture of 1-(2-Hydroxy-4-mercapto-3-propyl-phenyl)-ethanone (250 mg, 1.18 mmol), (S)-3-[(4-Iodomethyl-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]-benzonitrile (515 mg, 1.18 mmol) and cesium carbonate (769 mg, 2.36 mmol) in 2-butanone (10 ml) at room temperature under argon for 24 hours. Pour the mixture into water (85 ml) and extract with ethyl acetate (3×25 ml). Combine the organic extracts and wash with water, brine, then dry over sodium sulfate, filter and concentrate. Purify the crude product via silica chromatography eluting with 1:4 ethyl acetate:hexanes to give the title compound (325 mg, 53%). MS (m/z) 514 (M−H).

후처리

  1. extractionextract with ethyl acetate (3×25 ml)
  2. washCombine the organic extracts and wash with water, brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the crude product via silica chromatography
  7. washeluting with 1:4 ethyl acetate

출처 및 근거

ORD 기록
ord-41a2ef96ec9342f1919b0fe2009d806a
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803938B2

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