Triphenylphosphine → methyl 2-((S)-6-((2,2',6'-trimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 2280657Notes

Reaction equation

HRID 2280657 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][C@H:18]2[CH2:22][CH2:21][O:20][CH2:19]2)=[CH:12][C:11]=1[CH3:23].O[C:25]1[CH:38]=[CH:37][C:28]2[C@H:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=2[CH:26]=1.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>ClCCl>[CH3:1][C:2]1[C:7]([CH2:8][O:9][C:25]2[CH:38]=[CH:37][C:28]3[C@H:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=3[CH:26]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([CH3:23])=[CH:12][C:13]([O:17][C@H:18]2[CH2:22][CH2:21][O:20][CH2:19]2)=[CH:14][C:15]=1[CH3:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetateHCID 89701784HCID 89701784, compound

Product 1

HCID 89701783methyl 2-((S)-6-((2,2',6'-trimethyl-4'-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-(2,2′,6′-Trimethyl-4′-((tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methanol 12e (75 mg, 0.24 mmol), methyl (S)-2-(6-hydroxyl-2,3-dihydrobenzofuran-3-yl)acetate (50 mg, 0.24 mmol) and triphenylphosphine (94 mg, 0.36 mmol) were dissolved in 20 mL of dichloromethane. The reaction solution was cooled down to 0° C., followed by addition of diisopropyl azodicarboxylate (73 mg, 0.36 mmol), then warmed up to room temperature and stirred for 2 hours. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound methyl 2-((S)-6-((2,2′,6′-trimethyl-4′-(((S)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 12f (100 mg, yield 83.0%) as a white solid.

Workup

  1. temperaturewarmed up to room temperature
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-160d4505363a4dafb0174a0f59a71b07
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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