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Hydrochloric Acid → (4-{[tert-Butyl(dimethyl)silyl]oxy}-3,5-dipropylphenyl)methanol

HRID 5932
ノート
印刷プレビュー

反応式

HRID 5932 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:14][C:15]1[C:24]([CH2:25][CH2:26][CH3:27])=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][C:16]=1[CH2:28][CH2:29][CH3:30])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C(OCC)(=O)C.Cl>C1COCC1>[Si:7]([O:14][C:15]1[C:16]([CH2:28][CH2:29][CH3:30])=[CH:17][C:18]([CH2:19][OH:20])=[CH:23][C:24]=1[CH2:25][CH2:26][CH3:27])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9]
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

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 19385738Methyl 4-tert-butyldimethylsilyloxy-3,5-dipropylbenzoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19080464(4-{[tert-Butyl(dimethyl)silyl]oxy}-3,5-dipropylphenyl)methanol収率 92%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

Lithium aluminum hydride (9 mL of a 1M solution in THF) was added cautiously to a solution of the product of Step D at 0° C., and the reaction mixture was stirred overnight. Ethyl acetate was added to the mixture, cooled to 0° C. and treated with cold 1N HCl. After separating the organic phase, the aqueous phase was extracted with a mixture of ethyl acetate-ether-dichloromethane. The combined organic extracts were dried and concentrated. The concentrated material was purified by flash column chromatography using 20% ethyl acetate in hexane to afford 4.2 g (92%) of the title compound.

後処理

  1. customAfter separating the organic phase
  2. extractionthe aqueous phase was extracted with a mixture of ethyl acetate-ether-dichloromethane
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe concentrated material was purified by flash column chromatography

出典と根拠

ORDレコード
ord-fba0cb9fb1b145a1af2f772c0db3ce3a
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05246944

反応ノート

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