Sodium hydride → HCID 67354505, compound

HRID 1670819Notes

Reaction equation

HRID 1670819 reaction equation
[C:1]([Si:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:34][C:35]1[C:40]([Cl:41])=[CH:39][C:38]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:37][C:36]=1[Cl:50]>CN(C=O)C.C(OCC)C>[CH2:43]([O:42][C:38]1[CH:37]=[C:36]([Cl:50])[C:35]([CH2:34][N:15]2[CH2:16][CH2:17][CH:13]([CH:10]3[CH2:11][CH2:12][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:8][CH2:9]3)[C:14]2=[O:18])=[C:40]([Cl:41])[CH:39]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 57658010HCID 57658010, compoundHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene

Product 1

HCID 67354505HCID 67354505, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 3-[4-(tert-butyl-diphenyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (0.75 g, 1.78 mmol) in DMF (25 mL) with 60% sodium hydride (0.11 g, 2.67 mmol) and stir at room temperature for 15 minutes under N2. Cool the reaction to 0° C., treat with 2-bromomethyl-1,3-dichloro-5-benzyloxy-benzene (0.74 g, 2.13 mmol), and stir for 30 minutes at 0° C. Warm to room temperature and stir for 30 minutes under N2. Quench the reaction with water and dilute with diethyl ether. Wash the organic layer with water three times, dry (Na2SO4), and remove the solvent in vacuo to afford crude product. Purify with a 0 to 30% ethyl acetate in hexanes gradient to afford 1.2 g (99%) of the titled product. MS (m/z): 686 (M+).

Workup

  1. temperatureCool
  2. customthe reaction to 0° C.
  3. stirringstir for 30 minutes at 0° C
  4. temperatureWarm to room temperature
  5. stirringstir for 30 minutes under N2
  6. customQuench
  7. customthe reaction with water
  8. washWash the organic layer with water three times
  9. dry with materialdry (Na2SO4)
  10. customremove the solvent in vacuo
  11. customto afford crude product
  12. customPurify with a 0 to 30% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-be7b70417e124953823c768e374fc529
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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