Tributylphosphine → methyl [(3S)-6-({2',3',5',6'-tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

HRID 453459Notes

Reaction equation

HRID 453459 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]2[C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=2[CH:3]=1.[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][CH2:25][CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:20]([CH3:32])=[C:19]([CH3:33])[C:18]=1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40]O)[CH:35]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:33][C:19]1[C:20]([CH3:32])=[C:21]([O:24][CH2:25][CH2:26][CH2:27][S:28]([CH3:31])(=[O:30])=[O:29])[C:22]([CH3:23])=[C:17]([CH3:16])[C:18]=1[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][O:1][C:2]2[CH:15]=[CH:14][C:5]3[C@H:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][O:8][C:4]=3[CH:3]=2)[CH:35]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 59342583{2',3',5',6'-Tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

Product 1

HCID 59342570methyl [(3S)-6-({2',3',5',6'-tetramethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetateYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl [(3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl]acetate (0.208 g, 1.00 mmol), {2′,3′,5′,6′-tetramethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol (0.377 g, 1.00 mmol) and tributylphosphine (0.324 g, 1.60 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.404 g, 1.60 mmol) was added, and the mixture was stirred at room temperature for 1.5 hr under nitrogen atmosphere. Hexane (8 mL) was added to the reaction mixture, the precipitated insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20) to give the title compound (0.462 g, yield 82%) as a colorless oil.

Workup

  1. filtrationthe precipitated insoluble substance was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20)

Sources & evidence

ORD record
ord-79d8a2edb8cc49508d7ebac119c69a32
Source dataset
uspto-grants-2013_07
Patent number
US08492430B2

Reaction notes

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