Acetic Anhydride → HCID 131714017, compound

HRID 1607457Notes

Reaction equation

HRID 1607457 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-b66ac72724fc41d08b19ade9e9ee9fc9
Source dataset
uspto-grants-1989_09
Patent number
US04863934

Reaction notes

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