Tributylphosphine → HCID 117759798, compound

HRID 1049511Notes

Reaction equation

HRID 1049511 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=1[O:17][CH2:18][O:19][CH3:20].[CH:21]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37]O)[CH:32]=2)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:22]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH:21]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][O:16][C:13]3[CH:14]=[CH:15][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[C:11]([O:17][CH2:18][O:19][CH3:20])[CH:12]=3)[CH:32]=2)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoateHCID 117759877HCID 117759877, compound

Product 1

HCID 117759798HCID 117759798, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 2′-fluoro-5′-methoxy-2-(methoxymethoxy)biphenyl-4-ol (1.29 g), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (1.26 g) and tributylphosphine (2.3 mL) in toluene (30 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.32 g), and the mixture was stirred at room temperature for 50 hr. To the reaction mixture was added hexane, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.84 g) as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-29a94a810bb6474fb931b824f618601c
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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