Acetic Anhydride → HCID 131714003, compound

HRID 1153901Notes

Reaction equation

HRID 1153901 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[OH:25][CH:26]1[CH:31]([CH2:32][CH2:33][OH:34])[C:30]2[CH:35]=[CH:36][C:37]([C:39]([CH3:47])([CH3:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:38][C:29]=2[O:28][C:27]1([CH3:49])[CH3:48].C(N(CC)CC)C.[C:57](OC(=O)C)(=[O:59])[CH3:58]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH:6]=[CH:5][C:4]=1[OH:24].[C:57]([O:25][CH:26]1[CH:31]([CH2:32][CH2:33][OH:34])[C:30]2[CH:35]=[CH:36][C:37]([C:39]([CH3:47])([CH3:46])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:38][C:29]=2[O:28][C:27]1([CH3:48])[CH3:49])(=[O:59])[CH3:58]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 131714005HCID 131714005, compound

Product 1

HCID 131714003HCID 131714003, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3.48 g (0.01 mole) dl-5-hydroxy-4-(2-hydroxyethyl)-2,2-dimethyl-7-(1,1-dimethylheptyl)-3,4-dihydro-2H-benzopyran in 50 ml methylene chloride and containing 1.01 g (0.01 mole) triethylamine is cooled to 0° C. while stirring in a nitrogen atmosphere. To this is added a solution of 1.22 g (0.01 mole) 4-dimethylaminopyridine in 5 ml of methylene chloride followed by 1.02 g (0.01 mole) acetic anhydride. After stirring at 0°-5° C. for one hour, the mixture is allowed to warm to room temperature, extracted with methylene chloride and the extracts washed with sodium bicarbonate. After drying over anhydrous magnesium sulfate and evaporation of solvent, the desired product is obtained. It can be purified by column chromatography on silica gel if desired.

Workup

  1. stirringAfter stirring at 0°-5° C. for one hour
  2. temperatureto warm to room temperature
  3. extractionextracted with methylene chloride
  4. washthe extracts washed with sodium bicarbonate
  5. dry with materialAfter drying over anhydrous magnesium sulfate and evaporation of solvent

Sources & evidence

ORD record
ord-a33327ac1c044474862b82425d25b76a
Source dataset
uspto-grants-1984_12
Patent number
US04486428

Reaction notes

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