Triethylamine → HCID 86749123, compound

HRID 727506Notes

Reaction equation

HRID 727506 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]([O:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:15])/[CH2:11][CH2:12][CH2:13]I)=[O:4].C(N(CC)CC)C.[CH3:25][C:26](C)(C)[C:27](Cl)=O>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]([O:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:15])/[CH2:11][CH2:12][CH:13]=[C:26]([CH3:27])[CH3:25])=[O:4]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86749124HCID 86749124, compound

Product 1

HCID 86749123HCID 86749123, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 10.00 g (54.94 mmol) of Example 2 Part D alcohol in 50 mL of dichloromethane at 0° C. was added 0.67 g (5.50 mmol) of 4-dimethylaminopyridine (DMAP) and 11.49 mL (82.41 mmol) of triethylamine followed by the addition of 8.12 mL (65.93 mmol) of trimethylacetyl chloride over 15 min. The reaction mixture was stirred for 1 h at 0° C. and 2.5 h at room temperature. The suspension was diluted with 200 mL of dichloromethane and 300 mL of water. The layers were separated and the organic fraction was washed with solutions of KHSO4, NaHCO3 and NaCl, dried (MgSO4) and concentrated to provide title compound as a colorless liquid.

Workup

  1. customat 0° C.
  2. customThe layers were separated
  3. washthe organic fraction was washed with solutions of KHSO4, NaHCO3 and NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e250b9a17c7444ba94cc4cc0125142f2
Source dataset
uspto-grants-1998_01
Patent number
US05712396

Reaction notes

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