Bromotrichloromethane → HCID 20775653, compound

HRID 1815995Notes

Reaction equation

HRID 1815995 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[CH2:15][O:14][C:13]([CH:16]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])=[CH:25][CH:24]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.BrC(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]([C:11]1[N:12]=[C:13]([CH:16]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:32])[CH3:33])=[CH:27][CH:28]=2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[O:14][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20775652HCID 20775652, compound

Product 1

HCID 20775653HCID 20775653, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl (±)-3-[4-(benzyloxycarbonyl)-1,3-oxazolin-2-yl]-4-[4-(triisopropylsilyloxy)phenyl]butanoate (4.45 g, 8.03 mmole) in CH2Cl2 (40 mL) at 0° C. was added DBU (1.4 mL, 9.64 mmole), followed by bromotrichloromethane (0.95 mL, 9.64 mmole). The mixture was allowed to warm to RT as the bath warmed. After 18 hr the mixture was concentrated. The residue was chromatographed on silica gel (20% EtOAc/hexanes) to give the title compound (2.23 g, 50%) as a clear oil: MS (ES) m/e 552 (M+H)+.

Workup

  1. temperaturewarmed
  2. concentrationAfter 18 hr the mixture was concentrated
  3. customThe residue was chromatographed on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cdc4b5bcf733484785626020a0ea464a
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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