1-(tert-Butyldimethylsilyoxymethyl)-4-(2-decynyl)benzene → (4-Decylphenyl)methanol
Reaction equation
[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]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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##
Workup
- customThe organic layer was separated
- washwashed with two 50-mL portions of water
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-34b8b74230274ba7998114f7bf4e69fc
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05238832
Reaction notes
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