Chlorotrimethylsilane → HCID 14715012, compound

HRID 1030545Notes

Reaction equation

HRID 1030545 reaction equation
C(N(CC)CC)C.Cl[Si:9]([CH3:12])([CH3:11])[CH3:10].[CH:13]([O:16][C:17]1[C:18]([OH:27])([CH3:26])[C:19](=[O:25])[C:20]=1[O:21][CH:22]([CH3:24])[CH3:23])([CH3:15])[CH3:14]>C(OCC)C>[CH:13]([O:16][C:17]1[C:18]([O:27][Si:9]([CH3:12])([CH3:11])[CH3:10])([CH3:26])[C:19](=[O:25])[C:20]=1[O:21][CH:22]([CH3:23])[CH3:24])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14140277HCID 14140277, compound

Product 1

HCID 14715012HCID 14715012, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (28 mL, 0.20 mol) and chlorotrimethylsilane (13 mL, 0.10 mol) were successively added to a stirred solution of 3,4-diisopropoxy-2-hydroxy-2-methylcyclobut-3-ene-1-one (14.3 g, 0.0667 mol) in diethyl ether (250 mL). The mixture was allowed to stir at ambient temperatures for 18 hrs. The mixture was filtered through SiO2 contained in a sintered glass funnel. The filter cake was washed with additional diethyl ether. The ether was removed to leave 3,4-diisopropoxy-2-trimethylsilyloxy-2-methylcyclobut-3-ene-1-one (18 g, 94% yield) as a clear oil. Trimethylsilyl trifluoromethanesulfonate (150 μL, 0.78 mmol) was added to a stirred solution of the silyl ether (18 g, 0.0628 mol) and 1,2-bis(trimethylsilyloxy)ethane (16.2 mL, 0.066 mmol) in tetrahydrofuran (36 mL). The solution was stirred for 1 hr at 22° C. and additional trimethylsilyl trifluoromethanesulfonate (150 μL) was then added. The solution was stirred for an additional 0.25 hr and was concentrated to dryness. The residue was flash chromatographed on SiO2 (200 g) with diethyl ether-hexanes (1:1) to afford 2,2-ethylenedioxy-3-isopropoxy-4-methylcyclobut-3-ene-1-one (9 g, 73% yield) as a

Workup

  1. filtrationThe mixture was filtered through SiO2
  2. customcontained in a sintered glass funnel
  3. washThe filter cake was washed with additional diethyl ether
  4. customThe ether was removed

Sources & evidence

ORD record
ord-00771bfbba1a487e8c656e483b556fd1
Source dataset
uspto-grants-1992_04
Patent number
US05106842

Reaction notes

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