Triphenylphosphine → methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenoxy)acetate

HRID 1051107Notes

Reaction equation

HRID 1051107 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:30]=[C:29]3[C:25]([CH2:26][CH2:27][CH:28]3[OH:31])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:52]1[CH:53]=[C:54]([CH:61]=[CH:62][CH:63]=1)[O:55][CH2:56][C:57]([O:59][CH3:60])=[O:58]>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:30]=[C:29]3[C:25]([CH2:26][CH2:27][CH:28]3[O:31][C:52]3[CH:53]=[C:54]([CH:61]=[CH:62][CH:63]=3)[O:55][CH2:56][C:57]([O:59][CH3:60])=[O:58])=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10261746Methyl 2-(3-hydroxyphenoxy)acetateHCID 1181615566-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 118161559methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenoxy)acetateYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropyl azodicarboxylate (57 mg, 0.28 mmol) was added to a solution of 6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-ol (55 mg, 0.24 mmol), triphenylphosphine (97 mg, 0.37 mmol), methyl 2-(3-hydroxyphenoxy)acetate (37 mg, 0.20 mmol) and dichloromethane (2 mL) in a 50 mL round bottom flask at room temperature. After stirring overnight for 16 hours, the resulting mixture was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ethyl acetate (100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 38 mg (40%) of methyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenoxy)acetate.

Workup

  1. customthe resulting mixture was quenched with saturated aqueous NaHCO3 (50 mL)
  2. extractionextracted with ethyl acetate (100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude residue was purified by combiflash (4 g column, hexanes→100% ethyl acetate/hexanes, gradient)

Sources & evidence

ORD record
ord-fa0ef4d9662940ac90ea96a823d2f5a4
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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