Diethyl Ether → cis-4-(2-Tridecenyloxymethyl)phenylmethanol

HRID 2255022Notes

Reaction equation

HRID 2255022 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+].CCOCC>CC#N>[CH2:18]([O:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=1)/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 10526760cis-1-(tert-Butyldimethylsilyloxymethyl)-4-(2-tridecenyloxymethyl)benzene

Product 1

HCID 10829393cis-4-(2-Tridecenyloxymethyl)phenylmethanolYield 108.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of silyl ether (41) (341 mg, 0.84 mmol) in CH3CN (10 mL) was added 50% aqueous HF (1 mL) the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into saturated aqueous 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 (42) (290 mg, 98%) as a colorless oil: Rf 0.24 (9:1 petroleum ether/EtOAc); 1H NMR (CDCl3) δ 7.30 (s, 4 H), 5.60 (m, 2 H), 4.63 (s, 2 H), 4.49 (s, 2 H), 4.07 (d, J=5.1 Hz, 2 H), 239 (s, 2 H), 2.04 (q, J=6.6 Hz, 2 H), 1.27 (m, 16 H), 0.89 (t, J 6.6 Hz, 2 H); 13C NMR (CDCl3) δ 140.49, 137.82, 134.24, 128.10, 127.12, 125.94, 71.88, 65.85, 65.03, 32.03, 29.76, 29.66, 29.48, 29.37, 27.73, 22.82, 14.24. ##STR9##

Workup

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

Sources & evidence

ORD record
ord-314397e1413e40dcb4471168fcbc4d02
Source dataset
uspto-grants-1993_08
Patent number
US05238832

Reaction notes

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