Lactonitrile → HCID 70981387, compound

HRID 1409458Notes

Reaction equation

HRID 1409458 reaction equation
[C:1](#[N:5])[CH:2]([CH3:4])[OH:3].CCN(CC)CC.[Si:13](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[Si:13]([O:3][CH:2]([CH3:4])[C:1]#[N:5])([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6572LactonitrileHCID 8471TriethylamineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 70981387HCID 70981387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a flask containing DL-lactonitrile (36.3 mmol, 2.8 g) in DCM (25 ml), Et3N (54.7 mmol, 8.1 ml) and tert-butyldiphenylsilyl chloride (36.3 mmol, 10 g) were added. The resulting solution was stirred at RT for 24 h. The reaction mixture was quenched with H2O and extracted with DCM. The organic layer was washed with brine, dried, filtered and evaporated. The crude product was purified by flash-chromatography. Yield 4.52 g. 1H-NMR (400 MHz; CDCl3): δ 1.10 (s, 9H), 1.50 (d, 3H), 4.43 (q, 1H), 7.39-7.51 (m, 6H), 7.65 (d, 2H), 7.71 (d, 2H).

Workup

  1. additionwere added
  2. customThe reaction mixture was quenched with H2O
  3. extractionextracted with DCM
  4. washThe organic layer was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash-chromatography

Sources & evidence

ORD record
ord-11b116d6fe31480fb6a8ed9c6cb86a54
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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