Hydrochloric Acid → HCID 57838742, compound

HRID 2239219Notes

Reaction equation

HRID 2239219 reaction equation
[OH:1][CH:2]([CH3:15])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])=[O:5].N1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>>[C:23](=[O:24])([O:1][CH:2]([CH3:15])[CH2:3][C:4](=[O:5])[CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][CH:7]1[CH3:14])[O:25][CH2:26][CH3:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 67200945HCID 67200945, compound

Product 1

HCID 57838742HCID 57838742, compound

Procedure

A solution of 3-hydroxy-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone (8.0 mmol) in pyridine (1.85 g, 23.4 mmol) was treated at 0° C. with ethyl chloroformate (1.24 g, 23.4 mmol). The reaction solution was stirred at room temperature for 36 hours, treated with 5% aqueous HCl and extracted twice with ether, washed (H2O, saturated aqueous NaHCO3, then brine), dried over Na2SO4 and concentrated. The oil (2.38 g) was purified by flash-chromatography (cyclohexane/AcOEt=98:2), using SiO2 (100 g). Yield: 2.06 g (78%).

Workup

  1. extractionextracted twice with ether
  2. washwashed (H2O, saturated aqueous NaHCO3
  3. dry with materialbrine), dried over Na2SO4
  4. concentrationconcentrated
  5. customThe oil (2.38 g) was purified by flash-chromatography (cyclohexane/AcOEt=98:2)

Sources & evidence

ORD record
ord-8270cb1194a04a1aaf4e72e83395fb5e
Source dataset
uspto-grants-2010_05
Patent number
US07723286B2

Reaction notes

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