3-Cyclohexene-1-methanol → HCID 53968181, compound

HRID 1956382Notes

Reaction equation

HRID 1956382 reaction equation
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[C:18]([Si:22]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)Cl)([CH3:21])([CH3:20])[CH3:19]>CN(C)C1C=CN=CC=1>[Si:22]([O:8][CH:7]=[C:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 155123-Cyclohexene-1-methanolHCID 81531DiisopropylethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 53968181HCID 53968181, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
25 °C

Procedure

To a mixture of 3-cyclohexene-1-methanol (Aldrich, 13.0 mL, 0.11 mol), N,N-diisopropylethylamine (43 mL, 0.244 mol) and 4-dimethylaminopyridine (2.70 g., 0.022 mol) in 375 mL of dry CH2CI2 under N2 at 25° C. was added tert-butyldiphenylchlorosilane (32 mL, 0.123 mol). The mixture was stirred at 25° C. for 48 hours. The reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was loaded onto a 4"×4"column of silica and slowly eluted using hexanes as eluant. 3-(tert-butyldiphenylsilyloxymethylene)-1-cyclohexene, 33.6 g (86%), was obtained as a colorless oil which was homogenous by TLC (Rf=0.4, hexanes). Analytical calculated for C23H30OSi(0.3 H2O): C, 77.6; H 8.67. Found: C, 77.38; H, 8.72.

Workup

  1. washThe reaction mixture was washed sequentially with 150 mL portions of 1N HCl, water, brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was evaporated
  4. washslowly eluted

Sources & evidence

ORD record
ord-72c654ba06a34b18975f290902f9a24b
Source dataset
uspto-grants-1998_07
Patent number
US05780461

Reaction notes

Loading…