Sodium hydride → HCID 22461295, compound

HRID 1937629Notes

Reaction equation

HRID 1937629 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[NH:8][CH:7]=[CH:6][C:5]=2[C:4](=[O:11])[CH2:3]1.[H-].[Na+].[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>CN(C=O)C>[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[N:8]([Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:15]([CH3:17])[CH3:16])[CH:7]=[CH:6][C:5]=2[C:4](=[O:11])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 27522846,6-Dimethyl-1,5,6,7-tetrahydro-4H-indol-4-one

Product 1

HCID 22461295HCID 22461295, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-4-one (3.8 g, 23 mmol) in DMF (25 mL) was cooled to 0° C. and NaH (1.02 g of a 60% dispersion in mineral oil, 26 mmol) was added portionwise. The mixture was stirred for 30 min then triisopropylsilyl chloride (5.6 mL, 26 mmol) was added at 0° C. and stirring continued for 1 hr. The mixture was warmed to room temperature then extracted with ether (3×). The combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with isohexane: EtOAc (9:1), to give the title compound (2.9 g, 39%) as a colourless solid. 1H NMR (360 MHz, CDCl3) δ 1.11 (6H,s), 1.14 (18H,d, J 7.5 Hz) 1.51 (3H,heptet, J=7.5 Hz), 2.34 (2H,s), 2.71 (2H,s), 6.64 (1H,d, J=3.1 Hz), 6.71 (1H,d, J=3.1 Hz). MS (ES+) 320 (M+1).

Workup

  1. stirringstirring
  2. waitcontinued for 1 hr
  3. extractionthen extracted with ether (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with isohexane: EtOAc (9:1)

Sources & evidence

ORD record
ord-87cd5421709940e28087a37ea55a0cc2
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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