Sodium hydride → HCID 69224758, compound

HRID 902910Notes

Reaction equation

HRID 902910 reaction equation
[H-].[Na+].[C:3]1([C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].[Cl-].[NH4+]>CN(C=O)C.CCOCC>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][S:10][C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:32]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 84580Ethyl 5-bromovalerate

Product 1

HCID 69224758HCID 69224758, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (989 mg, 24.47 mmol) in anhydrous DMF (60 mL) was added portion wise triphenylmethanethiol. After 15 minutes of stirring, ethyl 5-bromovalerate (2.8 mL, 17.48 mmol) was injected and the mixture was stirred at ambient conditions for 24 h. The reaction mixture was portioned between ether and saturated ammonium chloride. The water phase was extracted several times with ether. The recombined organic layer was washed with brine, dried, filtered and evaporated. The crude was flashed using 5-10% ethyl acetate in hexanes. 1H-NMR(CDCl3, 400 MHz: 1.23(t, J=7.0 Hz, 3H); 1.42(m, 2H); 1.59(m, 2H); 2.16(m, 4H); 4.09(q, J=7.0 Hz, 2H), 7.21-7.30, 7.42(m, 15H).

Workup

  1. stirringthe mixture was stirred at ambient conditions for 24 h
  2. extractionThe water phase was extracted several times with ether
  3. washThe recombined organic layer was washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-116ca048a2ba46f5b0c5a43a63fdb997
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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