Triphenylphosphine → HCID 86604655, compound

HRID 1593548Notes

Reaction equation

HRID 1593548 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][OH:16])[O:8][C:7]([CH3:18])([CH3:17])[CH:6]=[C:5]2[C:19]([F:22])([F:21])[F:20].O[C:24]1[CH:38]=[CH:37][C:27]([O:28][C@@:29]([CH3:36])([CH2:34][CH3:35])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][O:16][C:24]1[CH:38]=[CH:37][C:27]([O:28][C@@:29]([CH3:36])([CH2:34][CH3:35])[C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1)[O:8][C:7]([CH3:18])([CH3:17])[CH:6]=[C:5]2[C:19]([F:20])([F:22])[F:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11996320(2S)-Methyl 2-(4-hydroxyphenoxy)-2-methylbutanoateHCID 68565082HCID 68565082, compound

Product 1

HCID 86604655HCID 86604655, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((6-chloro-2,2-dimethyl-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)propan-1-ol (0.5 g, 1.48 mmol), (2S)-Methyl 2-(4-hydroxyphenoxy)-2-methylbutanoate (0.35 g, 1.56 mmol), and triphenylphosphine (0.42 g, 1.6 mmol) in THF (20 mL) was added diethyl azodicarboxylate (0.28 g, 1.6 mmol) and the solution stirred at ambient temperature for 16 h. After concentrating under reduced pressure, the residue thus obtained was chromatographed over silica gel using AcOEt/hexanes to furnish the desired compound (0.49 g).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. customthe residue thus obtained
  3. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-a10bcdb3089840468c2930b41e0f2cb3
Source dataset
uspto-grants-2007_11
Patent number
US07297715B2

Reaction notes

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