tert-Butyldimethylsilyl chloride → tert-Butyl[(4,7-dimethyl-1H-inden-2-yl)oxy]dimethylsilane

HRID 650883Notes

Reaction equation

HRID 650883 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH3:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:11]=1[CH2:12][C:13](=[O:20])[CH2:14]2.C1CCN2C(=NCCC2)CC1>C1C=CC=CC=1.CCOCC>[O:20]([C:13]1[CH2:14][C:15]2[C:11]([CH:12]=1)=[C:10]([CH3:9])[CH:18]=[CH:17][C:16]=2[CH3:19])[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11535607HCID 11535607, compound

Product 1

HCID 21709881tert-Butyl[(4,7-dimethyl-1H-inden-2-yl)oxy]dimethylsilane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyldimethylchlorosilane (2.85 g, 18.9 mmol) and 4,7-dimethyl-2-indanone (2.53 g, 15.8 mmol, obtained by oxidation of 4,7-dimethylindene) in benzene (30 mL) was added DBU (3.13 g, 20.5 mmol) and the reaction mixture was stirred for 2 hours at room temperature. The mixture was diluted with Et2O (50 mL), washed with water (2×50 mL), 5% HCl (50 mL) water (2×50 mL) and dried over sodium sulphate. Evaporation of the solvents left a dark oil that was dissolved in pentane (30 mL). The unreacted starting materials were crystallized at −15° C. and removed by filtration. Evaporation of the solvent gave 3.03 g (69.9%) of fairly pure title compound as an orange oil. 1H NMR (CDCl3, δ): 6.94 (dq, 3J=7.7 Hz, 4J=0.3 Hz, 1H),; 6.78 (dq, 3J=7.7 Hz, 4J=0.3 Hz, 1H); 5.84 (t, 4J=1.1 Hz, 1H); 3.20 (m, 2H); 2.30 (s, 3H); 2.25 (s, 3H); 1.00 (s, 9H); 0.27 (s, 6H); 13C NMR (CDCl3, δ): 162.08; 143.39; 134.89; 129.45; 127.78; 125.49; 123.84; 105.28; 38.80; 25.65; 18.29; 18.21; −4.57.

Workup

  1. washwashed with water (2×50 mL), 5% HCl (50 mL) water (2×50 mL)
  2. dry with materialdried over sodium sulphate
  3. customEvaporation of the solvents
  4. waitleft a dark oil that
  5. dissolutionwas dissolved in pentane (30 mL)
  6. customThe unreacted starting materials were crystallized at −15° C.
  7. customremoved by filtration
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6155dab8018c4c8992760cc1d3236fa8
Source dataset
uspto-grants-2001_08
Patent number
US06277778B1

Reaction notes

Loading…