2-Fluoroethanol → HCID 123521878, compound

HRID 1893615Notes

Reaction equation

HRID 1893615 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:45])[C:11](=[O:44])[CH2:12][N:13]([C:33]1[C:42]([CH3:43])=[CH:41][C:36]2[C:37]([CH3:40])=[N:38][O:39][C:35]=2[CH:34]=1)[CH2:14][C:15]([NH:17][CH2:18][CH2:19][NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])(=[O:23])=[O:22])=[O:16].[F:46][CH2:47][CH2:48]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:45])[C:11](=[O:44])[CH2:12][N:13]([C:33]1[C:42]([CH3:43])=[CH:41][C:36]2[C:37]([CH3:40])=[N:38][O:39][C:35]=2[CH:34]=1)[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([CH2:48][CH2:47][F:46])[S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N+:30]([O-:32])=[O:31])(=[O:22])=[O:23])=[O:16]

Participants

7

Reactant 4

HCID 97372-FluoroethanolHCID 11776TriphenylphosphineHCID 66880968DIAD tolueneHCID 123943351HCID 123943351, compound

Product 1

HCID 123521878HCID 123521878, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (557 mg, 0.876 mmol) of step A, 2-fluoroethanol (84 mg, 1.31 mmol) and triphenylphosphine (345 mg, 1.31 mmol) were dissolved in tetrahydrofuran (4.4 ml), and the mixture was stirred at room temperature. Thereto was slowly added a 40% diisopropyl azodicarboxylate-toluene solution (0.70 ml), and the mixture was stirred at the same temperature for 12 hr. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over sodium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (561 mg, yield 94%) as a yellow solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 12 hr
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe solution was concentrated under reduced pressure
  6. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-03aae1b546764bd686dc40a6c6dc4ed0
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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