Hydrochloric Acid → HCID 68814860, compound

HRID 732853Notes

Reaction equation

HRID 732853 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])[C@@H:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH:9]=[CH:8][C@H: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 68814860HCID 68814860, compound

Procedure

A solution of 3-hydroxy-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-butanone (2.00 g, 84% pure, 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 aqueous 5% HCl and extracted twice with ether, washed with water, saturated aqueous NaHCO3, then with saturated aqueous NaCl, dried over Na2SO4 and concentrated. The oil thus obtained 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 with water, saturated aqueous NaHCO3
  3. dry with materialwith saturated aqueous NaCl, dried over Na2SO4
  4. concentrationconcentrated
  5. customThe oil thus obtained
  6. customwas purified by flash-chromatography (cyclohexane/AcOEt=98:2)

Sources & evidence

ORD record
ord-ba3361b115994f36aaf5c38421caacf3
Source dataset
uspto-grants-2009_09
Patent number
US07589055B2

Reaction notes

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