Ethyl Acetate → HCID 10279786, compound

HRID 2396260Notes

Reaction equation

HRID 2396260 reaction equation
[CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:5]=1[CH2:6]Br)([CH3:3])[CH3:2].[CH:18]([C:21]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]([CH3:36])[CH3:35])[C:22]=1[O:23][S:24]([N:27]=C=O)(=[O:26])=[O:25])([CH3:20])[CH3:19].[NH4+].[Cl-].C[CH2:40][O:41]C(C)=O>C1COCC1>[CH3:2][CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[C:8]([CH:15]([CH3:17])[CH3:16])[C:5]=1[CH2:6][C:40]([C:33]1[C:21]([CH:18]([CH3:19])[CH3:20])=[C:22]([O:23][S:24](=[O:25])(=[O:26])[NH2:27])[C:30]([CH:34]([CH3:35])[CH3:36])=[CH:31][CH:32]=1)=[O:41])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 10590086HCID 10590086, compoundHCID 10636716AG-G-92061

Product 1

HCID 10279786HCID 10279786, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4,6 - triisopropylbenzyl bromide (12 g, 40.4 mmol) in dry THF (160 mL) was added to a suspension of Mg powder (1.96 g, 80.8 mmol) (4hours) in THF (20 mL) heated under reflux. 2,6-Diisopropylphenoxysulfonyl isocyanate (ROSO2NCO) (see Phos. and Sulf., 19:167 (1984) for preparation) (11.45 g, 40.4 mmol) was added neat, and after the addition was completed, the reflux was continued for another 2 hours. The reaction was stirred at room temperature for 16 hours. Saturated NH4Cl and EtOAc were added. The EtOAc layer was separated, dried over MgSO4, filtered, and evaporated to dryness. After purification by column chromatography (4:1 hexane:EtOAc), the compound was isolated as white solid (13.5 g, 67%), mp 178°-180° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionafter the addition
  4. customThe EtOAc layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customAfter purification by column chromatography (4:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-898a7081a5bf4069ba210bb5a2d32642
Source dataset
uspto-grants-1996_02
Patent number
US05491172

Reaction notes

Loading…