Tributylphosphine → HCID 59364070, compound

HRID 1691534Notes

Reaction equation

HRID 1691534 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[O:15]=[S:16]1(=[O:39])[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36]O)[CH:31]=3)=[C:25]([CH3:38])[CH:24]=2)[CH2:18][CH2:17]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[O:15]=[S:16]1(=[O:39])[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][O:1][C:2]4[CH:3]=[CH:4][C:5]([CH:8]5[CH2:10][CH:9]5[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=4)[CH:31]=3)=[C:25]([CH3:38])[CH:24]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59342608{4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methanolHCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropane-1-carboxylate

Product 1

HCID 59364070HCID 59364070, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.156 g, 0.813 mmol), {4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.395 g, 0.739 mmol) and tributylphosphine (0.298 g, 1.47 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.372 g, 1.47 mmol) was added, and the mixture was stirred at room temperature for 4 hr. Hexane (15 mL) was added to the reaction mixture and the precipitated insoluble material was filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-40:60) to give the title compound (0.396 g, yield 91%) as a colorless oil.

Workup

  1. filtrationthe precipitated insoluble material was filtrated
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-40:60)

Sources & evidence

ORD record
ord-7a3856da796345259bc51ac9b977fe6b
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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