Tributylphosphine → HCID 23111742, compound

HRID 1163315Notes

Reaction equation

HRID 1163315 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][O:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 262953-Phenoxybenzyl alcoholHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23111808HCID 23111808, compound

Product 1

HCID 23111742HCID 23111742, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of ethyl 8-hydroxy-2,3,4,5-tetrahydro-1-benzoxepine-4-carboxylate (0.189 g, 0.800 mmol), 3-phenoxybenzyl alcohol (0.240 g, 1.20 mmol) and tributylphosphine (0.299 mL, 1.20 mmol) in toluene (8 mL) was stirred under ice-cooling. 1,1′-(Azodicarbonyl)dipiperidine (0.279 g, 1.20 mmol) was added by small portions, and the mixture was stirred under nitrogen atmosphere at room temperature for 8 hr. Hexane (4 mL) was added to the reaction mixture, and the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-20% ethyl acetate/hexane) to give the title compound (0.20 g, yield 60%) as a colorless oil.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (5%-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-266844d0576d4071968d9950360b664f
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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