Water → 4-[3-(t-Butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman

HRID 1792388노트

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HRID 1792388 반응식
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2(O)[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[S:19][CH2:18][CH:17]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].O>ClCCCl.[I-].[Zn+2].[I-]>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[S:19][CH2:18][CH:17]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 18770243HCID 18770243, 화합물

생성물 1

HCID 220333824-[3-(t-Butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3-(4-methoxyphenyl)thiochroman수율 61%

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 111,2-Dichloroethane용매

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온도
68 °C

실험 절차

To a solution of 4-[3-(t-butyldimethylsilyloxymethyl)phenyl]-7-methoxy-3 (4-methoxyphenyl)thiochroman-4-ol (619 mg, 1.184 mmol) in 1,2-dichloroethane (70 ml) were added zinc iodide (567 mg, 1.776 mmol) and sodium cyanoborohydride (558 mg, 8.88 mmol) and stirred at 68° C. for 2.5 hours. When the reaction was completed, water was added to the reaction mixture and extracted with ethyl acetate: The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was flash chromatographed on silica gel (n-hexane:ethyl acetate=8:2) to give 365 mg (yield: 61%, 3RS,4RS/3RS,4SR=6:1) of the title compound as a white solid. In this reaction, 260 mg (42%) of the unreacted starting compound was recovered.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed on silica gel (n-hexane:ethyl acetate=8:2)

출처 및 근거

ORD 기록
ord-7cf417c78fd8440aba2a5f7d3af6b5d0
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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