1-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene → (4-Decylphenyl)methanol

HRID 2255031노트

반응식

HRID 2255031 반응식
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C>C([O-])(O)=O.[Na+].CCOCC>[CH2:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

4

반응물 1

HCID 197395361-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene

생성물 1

HCID 13079698(4-Decylphenyl)methanol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 1-(tert-butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene (51) (313 mg, 0.87 mmol) in CH:CN (10 mL) was added 50% aqueous HF (1 mL), the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured in saturated NaHCO3 (50 mL) and ether (75 mL). The organic layer was separated and washed with two 50-mL portions of water, dried (MgSO4) and concentrated to yield the alcohol derivative. The latter was dissolved in EtOAc (10 mL) and 5% Pd/C was added. Hydrogen was then bubbled through the reaction mixture for 2 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to yield 4-decylphenylmethanol (52) is a clear oil; 1H NMR (CDCl3) δ7.28 (d, J=7.8 Hz, 2 H), 7.18 (d, J=8.1 Hz, 2 H), 4.65 (s, 2 H), 2.61 (t, J=7.8 Hz, 2 H), 1.83 (s, 1 H), 1.61 (m, 2 H), 1.25 (m, 16 H), 0.90 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 142.68, 138.25, 128.76, 127.27, 65.41, 35.80, 32.04, 31.69, 29.65, 29.75, 29.46, 26.06, 22.83, 14.27. ##STR26##

후처리

  1. customThe organic layer was separated
  2. washwashed with two 50-mL portions of water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-34b8b74230274ba7998114f7bf4e69fc
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05238832

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