Water → HCID 71279377, compound

HRID 2171024Notes

Reaction equation

HRID 2171024 reaction equation
[N:1]([CH2:4][C:5]1([CH2:8][O:9][C:10]2[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:11]=2[C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[CH2:22][CH2:23][C:24]3=[O:29])[CH2:7][CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][C:5]1([CH2:8][O:9][C:10]2[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:11]=2[C:20]2[CH:28]=[CH:27][CH:26]=[C:25]3[C:21]=2[CH2:22][CH2:23][C:24]3=[O:29])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 71279316HCID 71279316, compound

Product 1

HCID 71279377HCID 71279377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of 4-(2-((1-(azidomethyl)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one (1.5 g, 3.947 mmol) in tetrahydrofuran (50 mL), were added triphenylphosphine (4.14 g, 15.78 mmol) and the reaction mixture was stirred at RT for 2 h. water (5 mL) was added to the above reaction mixture and the resultant reaction was heated to 80° C. for 1 h. The reaction mixture was concentrated under reduced pressure and the obtained residue was acidified with 1N hydrochloric acid solution. Then extracted with ethyl acetate (3×) and the aq layer was basified with sodium bicarbonate solution and extracted with ethyl acetate and the combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afforded the title compound as a liquid.

Workup

  1. additionwas added to the above reaction mixture
  2. customthe resultant reaction
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionThen extracted with ethyl acetate (3×)
  5. extractionextracted with ethyl acetate
  6. washthe combined ethyl acetate layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae68cf5c4747408aaf4415e4dda6c351
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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