Acetone → HCID 19825353, compound

HRID 2249280Notes

Reaction equation

HRID 2249280 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.C([Li])[CH2:41][CH2:42][CH3:43].[CH3:45][C:46]([CH3:48])=[O:47].[Cl-].[NH4+].[O:51]1CCCC1>C(OCC)(=O)C.CCCCCC>[OH:51][C:42]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH:11]([O:22][Si:23]([C:36]([CH3:38])([CH3:39])[CH3:37])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:46]([OH:47])([CH3:48])[CH3:45])=[CH:17][CH:16]=2)=[CH:6][CH:7]=1)([CH3:43])[CH3:41]

Participants

8

Reactant 5

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 19825362HCID 19825362, compoundHCID 178418339Butyllithium

Product 1

HCID 19825353HCID 19825353, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Further, to a solution of 1.05 g (1.58 mmol) of 1,7-bis(4-bromophenyl)-4-(tert-butyldiphenylsiloxy)heptane in dry tetrahydrofuran (50 ml) was added a 1.60M hexane solution of n-butyllithium (2.15 ml, 3.44 mmol) in the atmosphere of argon, and the mixture was allowed to react at -78° C. for 30 min. To the solution was added 1.20 ml (16.3 mmol) of acetone, and the mixture was reacted at -78° C. for 10 min. followed by addition of a saturated aqueous solution of ammonium chloride and extraction with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol (100:1) yielded 728 mg (1.23 mmol) of 1,7-bis[4-(α-hydroxyisopropyl)phenyl]-4-(tert-butyldiphenylsiloxy)heptane.

Workup

  1. customto react at -78° C. for 30 min
  2. customthe mixture was reacted at -78° C. for 10 min.
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification
  7. washElution with dichloromethane-methanol (100:1)

Sources & evidence

ORD record
ord-c4112b9acaba4d5683ea57086a77d9e5
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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