Potassium bis(trimethylsilyl)amide → HCID 131729029, compound

HRID 1013376Notes

Reaction equation

HRID 1013376 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([N:18]1[CH2:25][CH:24]2[CH:20]([C:21](=O)[C:22]3[C:28]([CH3:29])=[CH:27][S:26][C:23]=32)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.C(Cl)Cl>[CH2:11]([N:18]1[CH2:25][CH:24]2[CH:20]([C:21](=[CH2:1])[C:22]3[C:28]([CH3:29])=[CH:27][S:26][C:23]=32)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 1317290282-Benzyl-6-methyl-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one

Product 1

HCID 131729029HCID 131729029, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyltriphenylphosphonium bromide (9.6 g, 26.8 mmol) was dissolved in THF (67 ml), cooled to 0° C. and treated with potassium bis(trimethylsilyl)amide (KHMDS) (5.33 g, 26.8 mmol) producing a clear yellow solution. Next, a solution of the product from step f) (1.9 g mg, 6.70 mmol) in THF (33 ml) was added and the reaction was warmed to 22° C. After 1 hour, the reaction was diluted with CH2Cl2 (300 ml) and washed with brine (100 ml). The organic layer was dried (MgSO4) and the solvent evaporated in vacuo to give the crude subtitle product (3.1 g) that was used without further purification.

Workup

  1. customproducing a clear yellow solution
  2. temperaturethe reaction was warmed to 22° C
  3. washwashed with brine (100 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-440c30647def41faa7cb4a7ced823984
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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