Imidazole → HCID 54053182, compound

HRID 1461398Notes

Reaction equation

HRID 1461398 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH:6]1[CH3:12].N1C=CN=C1.[C:18]([Si:22](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[CH3:21][C:18]([Si:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[O:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH:6]1[CH3:12])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 54017022HCID 54017022, compound

Product 1

HCID 54053182HCID 54053182, compoundYield 111.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 13.5 g (79.6 mmole) of the (3R)-3-(3-hydroxypropyl)-2-methylcyclohexanone in 240 ml of DMF was added 10.82 g (159.2 mmole) of imidazole followed by a dropwise addition of a solution of 26.2 g (95.3 mmole) of t-butylchlorodiphenyl silane in 25 ml of DMF. After addition, the solution was stirred at room temperature for 3 hours, quenched with 260 ml of iced water and extracted with 2×750 ml of ether. The combined etheral extracts were washed with 3×200 ml of water which was back extracted with 2×200 ml of ether. The combined etheral extracts were washed with brine, dried over MgSO4, filtered and concentrated to give 36.4 g of the crude (3R)-3-[3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-2-methylcyclohexanone which was used as such. An analytical sample was obtained by further purification of the above crude on a silica gel column (20:1, hexane/EtOAc). IR (CHCl3 ): 1130, 1700, 2850 cm-1. 1H NMR: δ0.98-1.05 (m, 12H), 1.15-1.70 (m, 7HO, 1.89 (m, 2H), 2.05 (m, 1H), 2.15 (m, 1H), 2.25 (m, 1H), 2.40 (m, 1H), 2.55 (m, 1H), 3.65 (m, 2H), 7.38 (m, 6H), 7.66 (m, 4H). Mass spectrum: M+ -CH3 (393). Anal. for C26H36O2Si: Calc. for C, 76.42; H, 8.88; Si, 6.87. Found: C, 76.16; H, 9.11; Si, 6.98.

Workup

  1. additionAfter addition
  2. customquenched with 260 ml of iced water
  3. extractionextracted with 2×750 ml of ether
  4. washThe combined etheral extracts were washed with 3×200 ml of water which
  5. extractionwas back extracted with 2×200 ml of ether
  6. washThe combined etheral extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-48684c1403e1470ca7f50b82ae778505
Source dataset
uspto-grants-1991_12
Patent number
US05075327

Reaction notes

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