tert-Butanol → HCID 15674615, compound

HRID 1937121Notes

Reaction equation

HRID 1937121 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[C:7]([OH:11])(C)(C)C.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:24]([OH:33])[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26]>C1COCC1.O>[C:7](=[O:11])([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])[O:33][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 68490alpha-HydroxyacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15674615HCID 15674615, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (0.543 g, 4.83 mM) and t-butyl alcohol (0.525 g, 7.08 mM) were stirred in 15 mL dry THF. The mixture was added to a suspension of carbonyldiimidazole (1.5 g, 9.26 mM) in 15 mL dry THF. The mixture was stirred at room temperature for about 14 h. Phenacyl alcohol (0.643 g, 4.73 mM) was added to the reaction mixture and stirred at 0° C. for 2 h. About 30 mL water was added to the mixture and the carbonate was extracted with (3×50 mL) dichloromethane. The carbonate was purified using 4:1 hexane ethyl acetate. Yield 0.429 g (38%) from 0.643 g phenacyl alcohol, yellow oil; 1H NMR (CDCl3, 400 MHz) δ1.50 (s, 9H), 5.23 (s, 2H), 7.43-7.59 (m, 3H), 7.88 (d, J=7 Hz, 2); 13C NMR (CDCl3, 400 MHz) δ192.3, 153.1, 134.1, 133.9, 128.8, 127.7, 83.0, 67.9, 27.7; FAB-MS, m/z (rel. intensity) 237 (M+1, 13),181 (100), 163 (14), 119 (21), 105 (49), 91 (21), 77 (9), 57 (73); HRMS calcd for (M+1) C13H17O4; 237.1127, found: 237.1135.

Workup

  1. stirringstirred at 0° C. for 2 h
  2. extractionthe carbonate was extracted with (3×50 mL) dichloromethane
  3. customThe carbonate was purified

Sources & evidence

ORD record
ord-a45627c57b084d0d9d69fbe31c849b24
Source dataset
uspto-grants-2002_05
Patent number
US06392089B1

Reaction notes

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