Tetrahydrofuran → HCID 10174371, compound

HRID 1297750Notes

Reaction equation

HRID 1297750 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si](C(C)(C)C)(C)C)=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40])(C)(C)C.CC(C)([O-])C.[K+].C1COCC1.[CH3:54][O:55][C:56]1[CH:63]=[CH:62][C:59]([CH2:60]Cl)=[CH:58][CH:57]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.O>[OH:31][C:27]1[C:26]([CH3:39])=[CH:25][C:24]([C:14]2([C:10]3[CH:9]=[C:8]([CH3:40])[C:7]([OH:6])=[C:12]([CH3:13])[CH:11]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH2:60][C:59]3[CH:62]=[CH:63][C:56]([O:55][CH3:54])=[CH:57][CH:58]=3)[C:15]2=[O:23])=[CH:29][C:28]=1[CH3:30]

Participants

8

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 699934-Methyloxybenzyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 58914719HCID 58914719, compound

Product 1

HCID 10174371HCID 10174371, compoundYield 130.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve 3,3-bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (150 mg, 0.25 mmol) in anhydrous DMF (1.5 mL) under nitrogen. Add slowly a 1M solution of potassium t-butoxide in THF (0.260 mL, 0.260 mmol). Stir 5 min and add 4-methoxybenzyl chloride (0.037 mL, 0.275 mmol). After 1 h add a 1M solution of tetrabutylammonium fluoride in THF (0.625 mL, 0.625 mmol) and stir 2 h. Dilute with water (10 mL) and extract with ethyl acetate (3×15 mL). Wash combined organic portions with water, brine, dry (Na2SO4), filter and concentrate in vacuo to obtain 161 mg of a residue. Recrystallize from CH2Cl2 and hexane to obtain 63 mg (51%) of the title compound as a white solid. MS (ES): m/z=494 (M+1), 492 (M−1); 1H NMR(DMSO-d6): δ8.24 (s, 2H), 7.30-7.20 (m, 4H), 7.04 (m, 2H), 6.89 (d, J=8.7 Hz, 2H), 6.68 (s, 4H), 5.77 (s, 2H), 3.72 (s, 3H), 2.07 (s, 12H).

Workup

  1. stirringstir 2 h
  2. extractionextract with ethyl acetate (3×15 mL)
  3. washWash
  4. dry with materialdry (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b341ead7136445aba61291f88559b22a
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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