2-Fluoroethanol → HCID 58086797, compound

HRID 253424Notes

Reaction equation

HRID 253424 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9]([OH:16])=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])=[C:4]([F:19])[CH:3]=1.[F:20][CH2:21][CH2:22]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>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9]([O:16][CH2:22][CH2:21][F:20])=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])=[C:4]([F:19])[CH:3]=1

Participants

8

Reactant 4

HCID 97372-FluoroethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 58086862HCID 58086862, compound

Product 1

HCID 58086797HCID 58086797, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-chloro-2-fluoro-benzyloxy)-2-hydroxy-benzaldehyde (93, yyyyl40 mg, 0.5 mmol, prepared by protocol of Example 21, Steps 1 and 2 of Scheme 20, using 4-chloro-2-fluoro-benzyl bromide in place of 4-chloro-benzyl bromide in Step 1) in tetrahydrofuran (8 mL) was added dropwise a mixture of 2-fluoro-ethanol (64 mg, 1.0 mmol), triphenylphosphine (180 mg, 0.7 mmol), and diisopropyl azodicarboxylate (120 mg, 0.6 mol) in tetrahydrofuran (5 ml) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes and then at 40° C. for 3 days. The reaction mixture was dissolved in water and ethyl acetate. The organic layers were collected, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexanes to provide the compound as a white solid (94, 88 mg, 54%). MS (ESI) [M+H+]+=327.12.

Workup

  1. waitat 40° C. for 3 days
  2. customThe organic layers were collected
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ffaa3ddcd600436d88d60058d70b0a0b
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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