Tetrahydrofuran → HCID 58979125, compound

HRID 1181122Notes

Reaction equation

HRID 1181122 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30]O)([CH3:4])([CH3:3])[CH3:2].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:58]>CCOC(C)=O>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][Br:58])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58979414HCID 58979414, compound

Product 1

HCID 58979125HCID 58979125, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 100 mL round bottomed flask was charged with 3-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (1.0 g, 2.29 mmol), anhydrous THF (25 mL), and then triphenylphosphine (1.20 g, 4.57 mmol) and CBr4 (1.52 g, 4.57 mmol). The yellow mixture was stirred at ambient temperature under a nitrogen atmosphere for 1 h and was poured into EtOAc (100 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated. The crude product was purified using radial chromatography (EtOAc:hexanes 15:85 to 25:75) to give a colorless oil (0.95 g, 83%). MS (ES) m/e 501 (M+1).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-11bb9f52e24249d08758b5d497d3923e
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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