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Tetrahydrofuran → Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane

HRID 1263522
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HRID 1263522 반응식
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[Si:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:18]=[CH:17][C:16]=1C1CCC(=O)CC1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].O1C[CH2:39][CH2:38][CH2:37]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:10]([Si:7]([O:14][C:15]1[CH:20]=[C:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:18]=[CH:17][C:16]=1[CH:38]1[CH2:39][CH2:3][C:2](=[CH2:5])[CH2:1][CH2:37]1)([CH3:8])[CH3:9])([CH3:13])([CH3:12])[CH3:11]
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5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 17946008Tert-butyl[5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methylenecyclohexyl)phenoxy]dimethylsilane수율 93%

시약·촉매·용매 1

HCID 74505
Methyltriphenyliphosphonium bromide
촉매

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온도
0 °C

실험 절차

To a round bottomed flask was added methyltriphenylphosphonium bromide (0.99 g) and tetrahydrofuran (30 ml). The resulting suspension was cooled to 0° C. and potassium tert-butoxide (0.31 g) was added in one portion. The resulting solution was stirred at 0° C. for 0.5 hr, then 4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanone (0.60 g) added as a solution in tetrahydrofuran (10 ml). The solution was stirred for 1 hr at 0° C., then allowed to warm to room temperature and stirred for 15 hr. The reaction mixture was partitioned between ethyl acetate (20 ml) and saturated ammonium chloride solution (20 ml). The layers were separated and the aqueous layer extracted with ethyl acetate (2×20ml). The combined organic phases were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:9 v/v) furnished the title compound (0.56 g, 93%) as a colourless oil. δH (CDCl3): 0.17 (6H, s), 0.24 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.34-1.47 (2H, m), 1.86-1.94 (2H, m), 2.10-2.20 (2H, m), 2.35-2.43 (2H, m), 3.00 (1H, tt), 4.64 (2H, m), 6.29 (1H, d), 6.39 (1H, dd), 6.94 (1H, d).

후처리

  1. stirringThe solution was stirred for 1 hr at 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 15 hr
  4. customThe reaction mixture was partitioned between ethyl acetate (20 ml) and saturated ammonium chloride solution (20 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with ethyl acetate (2×20ml)
  7. washThe combined organic phases were washed with brine (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:9 v/v)

출처 및 근거

ORD 기록
ord-febb2b31876a47a9887df777cfff491d
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06541473B2

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