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

HRID 2255031ノート

反応式

HRID 2255031 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 13079698(4-Decylphenyl)methanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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##

後処理

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

出典と根拠

ORDレコード
ord-34b8b74230274ba7998114f7bf4e69fc
出典データセット
uspto-grants-1993_08
特許番号
US05238832

反応ノート

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