Sodium bis(trimethylsilyl)amide → HCID 22472035, compound

HRID 1071223Notes

Reaction equation

HRID 1071223 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH:17]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:16]2=[O:31].[C:32]1([Li])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1>[OH:22][C:18]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:19]2[C:15](=[CH:14][C:13]([O:12][CH3:11])=[CH:21][CH:20]=2)[C:16](=[O:31])[CH:17]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.[OH:31][C:16]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([O:12][CH3:11])[CH:14]=2)[C:18](=[O:22])[CH:17]1[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 15882768HCID 15882768, compoundHCID 178506676HCID 178506676, compound

Product 2

HCID 22472035HCID 22472035, compoundHCID 22472041HCID 22472041, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium bis(trimethylsilyl) amide (0.6 N, 7.09 mL, 4.25 mmol) was added dropwise into a cold (0° C.) mixture of 5-methoxy-2-(4-methoxyphenyl)-1H-inden-1,3(2H)-dione (1000 mg, 3.54 mmol) and tetrahydrofuran (15 mL). The mixture was allowed to stir for 1.0 h. Phenyl lithium (4.13 mL, 7.44 mmol) was added dropwise into the mixture at 0° C. The reaction mixture was allowed to warm to RT and stirred for 2 h. The reaction was quenched with 2 N HCl, poured into water, and extracted with ethyl acetate. The organic extracts were washed with brine and dried over MgSO4. Evaporation and flash chromatography (30%-50% ethyl acetate/petroleum ether) gave 3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-3-phenyl-indan-1-one as a light red foam and 3-hydroxy-5-methoxy-2-(4-methoxyphenyl)-3-phenyl-indan-1-one as a light orange solid: mp 68-70; MS m/e 361 (M+H)+.

Workup

  1. stirringstirred for 2 h
  2. customThe reaction was quenched with 2 N HCl
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. customEvaporation and flash chromatography (30%-50% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-f5fc29f1009c4d8bad4ef80d777f1530
Source dataset
uspto-grants-2005_06
Patent number
US06903238B2

Reaction notes

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