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

HRID 1263522
ノート
印刷プレビュー

反応式

HRID 1263522 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 223378144-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 74505
Methyltriphenyliphosphonium bromide
触媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-febb2b31876a47a9887df777cfff491d
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06541473B2

反応ノート

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