2-Indanone → HCID 21709892, compound

HRID 650882Notes

Reaction equation

HRID 650882 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1.[CH2:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][C:31]1=[O:39]>C1C=CC=CC=1.CCOCC>[O:39]([C:31]1[CH2:32][C:33]2[C:38]([CH:30]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2)[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 119832-IndanoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 21709892HCID 21709892, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyldiphenylchlorosilane (42.43 g, 154.4 mmol) and DBU (25.64 g, 168.4 mmol) in benzene (200 mL) was added 2-indanone (18.38 g, 139.1 mmol) in one portion. The reaction mixture was stirred overnight, diluted with Et2O (200 mL), washed with 10% HCl (2×200 mL) and water (2×200 mL) and dried over sodium sulfate. The solvents were evaporated to leave a dark brown oil. Distillation under reduced pressure gave 38.22 g (74.1%) of the title compound as a yellow oil (bp. 172-175° C./0.05 mbar). 1H NMR (CDCl3, δ): 7.77-7.74 (m, 4H); 7.46-7.36 (m, 6H) 7.18-7.16 (m, 1H); 7.11-7.07 (m, 1H); 6.98-6.94 (m, 2H); 5.48 (d, 4J=0.7 Hz, 1H); 3.29 (s, 2H); 1.09 (s, 9H). 13C NMR (CDCl3, δ): 162.13; 145.17; 136.75; 135.53; 132.43; 130.20; 127.99; 126.51; 123.15; 122.49; 119.24; 107.91; 39.43; 26.60; 19.46.

Workup

  1. washwashed with 10% HCl (2×200 mL) and water (2×200 mL)
  2. dry with materialdried over sodium sulfate
  3. customThe solvents were evaporated
  4. customto leave a dark brown oil
  5. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-5b234ae01bee417b8d9206ad7853a6bd
Source dataset
uspto-grants-2001_08
Patent number
US06277778B1

Reaction notes

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