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Sodium Bicarbonate → tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]-3-cyclohexen-1-yl}phenoxy) dimethylsilane

HRID 2307127
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HRID 2307127 반응식
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:20][CH2:19][C:18]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][C:23]=3[O:32][CH2:33][O:34][CH3:35])(O)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:4]([Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH2:20][CH2:19][C:18]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][O:30][CH3:31])=[CH:24][C:23]=3[O:32][CH2:33][O:34][CH3:35])=[CH:17][CH2:16]2)=[CH:13][CH:14]=1)([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]
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참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 538169184-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-1-[2,4-bis(methoxymethoxy)phenyl]cyclohexanol

생성물 1

HCID 22337758tert-Butyl(4-{4-[2,4-bis(methoxymethoxy)phenyl]-3-cyclohexen-1-yl}phenoxy) dimethylsilane

시약·촉매·용매 1

HCID 1140Toluene
용매

실험 절차

A round bottomed flask equipped with magnetic stirrer was charged with 4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-[2,4-bis(methoxymethoxy) phenyl]cyclohexanol (125 mg, 0.25 mmol), toluene (10 ml) and p-toluene sulfonic acid monohydrate (3 crystals). The reaction mixture was heated to reflux temperature for 30 min, then cooled to room temperature before adding saturated aqueous sodium bicarbonate (5 ml). The layers were separated and the aqueous layer was extracted with ethyl acetate (3×10 ml). The combined organic layers were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The title compound was isolated without further purification as an oil (118 mg, 98%) and a mixture of diastereoisomers. δH(CDCl3) 0.19 (6H, s), 0.98 (9H, s), 1.84 (1H, m), 2.00 (1H, m), 2.27 (1H, m), 2.44 (2H, m), 2.56 (1H, m), 3.48 (3H, s), 3.49 (3H, s), 5.15 (2×2H, s), 5.79 (1H, m), 6.67 (1H, dd), 6.77 (2H, d), 6.78 (1H, d), 7.07 (2H, d), 7.11 (1H, d).

후처리

  1. customA round bottomed flask equipped with magnetic stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux temperature for 30 min
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×10 ml)
  6. washThe combined organic layers were washed with brine (10 ml)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-112c46ef63d04c179be660c3a925f1c4
출처 데이터셋
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06828460B2

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