Formaldehyde → [4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanol

HRID 606545

반응식

HRID 606545 반응식
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1.[CH2:27]=[O:28]>CCCCC.C1COCC1>[Si:20]([O:19][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:27][OH:28])=[CH:8][CH:9]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 67046104[4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanol수율 69%

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyllithium (6.6 mL of a 1.7 M solution in pentane, 11.32 mmol) was added to a solution of the aryl bromide 7 (2.0 g, 5.39 mmol) in THF (22 mL) at −78° C. After 0.5 h paraformaldehyde (323 mg, 8.09 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 6:1 hex/EtOAc) yielded 1.2 g (69%) of the alcohol 8 as a clear, colorless oil.

후처리

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-67fbe19536ed4065ad1c29c3c4d64a78
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915316B2

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