Acetic Anhydride → HCID 131714017, compound

HRID 2118914Notes

Reaction equation

HRID 2118914 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][C:26]1([CH2:50][CH2:51][CH2:52][OH:53])[CH2:31][C:30]2[CH:32]=[CH:33][C:34]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH3:38])=[CH:35][C:29]=2[O:28][C:27]1([CH3:49])[CH3:48].C(N(CC)CC)C.[C:61](OC(=O)C)(=[O:63])[CH3:62]>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:61]([O:25][C:26]1([CH2:50][CH2:51][CH2:52][OH:53])[CH2:31][C:30]2[CH:32]=[CH:33][C:34]([O:36][CH:37]([CH2:39][CH2:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH3:38])=[CH:35][C:29]=2[O:28][C:27]1([CH3:48])[CH3:49])(=[O:63])[CH3:62]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 131714019HCID 131714019, compound

Product 1

HCID 131714017HCID 131714017, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3.177 g (7.96 mmole) dl-5-hydroxy-3-(3-hydroxypropyl)-2,2-dimethyl-7-(5-phenyl-2-pentyloxy)-3,4-dihydro-2H-benzopyran in 40 ml methylene chloride, under a nitrogen atmosphere, was added 805 mg (7.96 mmole) triethylamine, the mixture stirred for 15 minutes and cooled to 0° C. At this temperature, 970 mg (7.79 mmole) 4-dimethylaminopyridine in 3 ml methylene chloride followed by 813 mg (7.96 mmole) acetic anhydride was added and the resulting mixture stirred at 0°-5° C. for one hour. After allowing the mixture to warm to room temperature, it was extracted three times with 30 ml portions methylene chloride. The extracts were washed with saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to obtain 4.158 g of crude oil. The crude product was purified by column chromatography on silica gel eluting with ethyl ether/methylene chloride 3:97 (v/v) for 7 fractions and 1:9 (v/v) for 43 fractions. Fractions 18-27 contained the diacetate. Fractions 28-45 containing desired monoacetate were combined and evaporated to afford 1.823 g of the title compound. 1H-NMR(CDCl3)ppm(delta): 2.20 (s, 3H), 3.50 (t, 2H), 6.20 (m, 2H), 7.10 (s, 5H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture stirred at 0°-5° C. for one hour
  3. temperatureto warm to room temperature
  4. extractionit was extracted three times with 30 ml portions methylene chloride
  5. washThe extracts were washed with saturated sodium bicarbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto obtain 4.158 g of crude oil
  9. customThe crude product was purified by column chromatography on silica gel eluting with ethyl ether/methylene chloride 3:97 (v/v) for 7 fractions and 1:9 (v/v) for 43 fractions
  10. customevaporated

Sources & evidence

ORD record
ord-3fb5641cced04e9e81f228bc600308fe
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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