Hydrochloric Acid → HCID 131714011, compound

HRID 1905125Notes

Reaction equation

HRID 1905125 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH:12]=[CH:11][C:10]=1[OH:30].C([O:34][CH:35]1[CH:40]([CH2:41][CH:42]([OH:44])[CH3:43])[C:39]2[CH:45]=[CH:46][C:47]([C:49]([CH3:57])([CH3:56])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:38]=2[O:37][C:36]1([CH3:59])[CH3:58])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][NH:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH:12]=[CH:11][C:10]=1[OH:30].[OH:34][CH:35]1[CH:40]([CH2:41][C:42](=[O:44])[CH3:43])[C:39]2[CH:45]=[CH:46][C:47]([C:49]([CH3:57])([CH3:56])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][C:38]=2[O:37][C:36]1([CH3:58])[CH3:59]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10340Sodium CarbonateHCID 131714013HCID 131714013, compound

Product 1

HCID 131714011HCID 131714011, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5.0 g (0.02 mole) chromic anhydride in 5.0 ml water is added with stirring and ice cooling to 50 ml pyridine. To this is added at 10° C. 4.04 g (0.01 mole) dl-5-acetoxy-4-(2-hydroxypropyl)-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran and the resulting mixture stirred at room temperature for three hours. The reaction mixture is poured into water, made alkaline (pH 8.5-9.0) with sodium carbonate, stirred for 20 minutes then acidified with dilute hydrochloric acid and extracted with methylene chloride. The organic layer is washed with sodium bicarbonate solution, water, brine, dried over magnesium sulfate and the solvent evaporated, the last of the solvent being removed in vacuo. The residue is purified by column chromatography on silica gel to obtain the desired ketone.

Workup

  1. additionTo this is added at 10° C
  2. stirringstirred for 20 minutes
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with sodium bicarbonate solution, water, brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated
  7. customthe last of the solvent being removed in vacuo
  8. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-933408fe030e4393a6999a0455d24052
Source dataset
uspto-grants-1989_06
Patent number
US04841078

Reaction notes

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