Water → HCID 86597998, compound

HRID 2101245Notes

Reaction equation

HRID 2101245 reaction equation
[C:1](=[O:12])([S:9][CH2:10][CH3:11])[O:2][O:3][CH:4](Cl)[CH:5]([CH3:7])[CH3:6].[C:13]([OH:19])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].C(N(CC)C(C)C)(C)C.O>CCOCC>[C:1](=[O:12])([S:9][CH2:10][CH3:11])[O:2][O:3][CH:4]([O:19][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6417Pivalic acidHCID 81531DiisopropylethylamineHCID 86597999HCID 86597999, compound

Product 1

HCID 86597998HCID 86597998, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of (44) (936 mg, 4.76 mmol), pivalic acid (2.43 g, 23.8 mmol) and N,N-diisopropylethylamine (2.40 g, 23.8 mmol) was stirred at 75° C. for four days, and the reaction was judged complete by 1H-NMR. The reaction mixture was cooled to room temperature and portioned between water and ether, the ether phase was washed successively with water, aqueous NaHCO3, and brine, then dried over anhydrous Na2SO4. After rotary evaporation, the crude O-(1-pivaloyloxyisobutoxy) S-ethyl thiocarbonate (45) was obtained in quantitative yield, and used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): δ 0.96 (d, 6H), 1.21 (d, 9H), 1.30 (t, 3H), 2.03 (m, 1H), 6.65 (d, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe ether phase was washed successively with water, aqueous NaHCO3, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customAfter rotary evaporation

Sources & evidence

ORD record
ord-178af6967d844749875cace7b192550f
Source dataset
uspto-grants-2009_08
Patent number
US07572830B2

Reaction notes

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