Sodium Hydroxide → t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

HRID 1378840

반응식

HRID 1378840 반응식
[Si:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH:18]=[CH2:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B.C1C[O:27]CC1.[O-][O-].[Na+].[Na+].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][C:9]1[C:10]([CH2:20][CH2:21][CH3:22])=[CH:11][C:12]([CH2:18][CH2:19][OH:27])=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 14803Sodium peroxideHCID 2723981Borane;tetrahydrofuranHCID 19080390t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene

생성물 1

HCID 19080442t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 475 mg (1.48 mmol) of the product of Step B in 3 mL of THF at 0 ° C. was added 1.6 mL (1.62 mmol) of a 1N borane/THF solution. After 1 hour TLC indicated that the starting material had been consumed. The reaction mixture was quenched with 3 drops of methanol and then 0.70 mL (6.22 mmol) of 30% sodium peroxide and 6.2 mL (6.2 mmol) of 1N sodium hydroxide were added. After two hours the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was then dried over sodium sulfate, filtered and concentrated. Hash chromatography (silica gel, hexane/ethyl acetate 4:1) gave 265 mg of the title compound as a clear oil.

후처리

  1. customhad been consumed
  2. customThe reaction mixture was quenched with 3 drops of methanol
  3. washwashed with water and brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-be54b93fb24b49eda2c4342074f1c3ce
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05668176

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