Triphenylphosphine → 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

HRID 2171018Notes

Reaction equation

HRID 2171018 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][C:16]2=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:55]([Si:59]([CH2:72][O:73][C:74]1([CH2:77]O)[CH2:76][CH2:75]1)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([CH3:58])([CH3:57])[CH3:56]>O1CCCC1>[Si:59]([CH2:72][O:73][C:74]1([CH2:77][O:1][C:2]2[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=2[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][CH2:15][C:16]3=[O:21])[CH2:76][CH2:75]1)([C:55]([CH3:58])([CH3:56])[CH3:57])([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67465035{1-[(tert-Butyl-diphenyl-silanyl)-methoxy]-cyclopropyl}-methanolHCID 674668064-(2-Hydroxy-3,4-dimethoxy-phenyl)-indan-1-one2×

Product 1

HCID 712796704-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 4-(2-hydroxy-3,4-dimethoxy-phenyl)-indan-1-one (Compound 303) (5 g, 17.60 mmol) in tetrahydrofuran (50 mL), were added triphenylphosphine (9.2 g, 35.21 mmol) and diisopropylazodicarboxylate (7.11 g, 35.21 mmol) and {1-[(tert-Butyl-diphenyl-silanyl)-methoxy]-cyclopropyl}-methanol (7.18 g, 21.12 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) afforded 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one as a liquid.

Workup

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (silica gel, 0-10% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-f63d104c45934287be6ae7e243660e18
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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