Diethyl Ether → HCID 53956501, compound

HRID 2232482Notes

Reaction equation

HRID 2232482 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C:7]1([CH3:21])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([OH:20])=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].CCOCC>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C:7]1([CH3:21])[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][C:15]([O:20][C:23](=[O:25])[CH3:24])=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]=2[O:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 7918Acetic AnhydrideHCID 54553078HCID 54553078, compound

Product 1

HCID 53956501HCID 53956501, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 0.8 g of racemic-3,4-dihydro-7-hydroxy-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester in 8 ml of pyridine was added 0.37 ml of acetic anhydride. The solution was stirred at room temperature for 5 hours then poured into ice-water and worked up with ether in the usual manner (the combined ether extracts were additionally washed with 1N hydrochloric acid and saturated sodium bicarbonate solutions). The oily product (1.0 g) was chromatographed on 50 g of silica gel. Elution with 19:1 toluene-ethyl acetate afforded 0.575 g (63.3%) of racemic-7-acetoxy-3,4-dihydro-2-methyl-8-n-propyl-2H-1-benzopyran-2-propanoic acid ethyl ester as a pale-yellow oil.

Workup

  1. washwere additionally washed with 1N hydrochloric acid and saturated sodium bicarbonate solutions)
  2. customThe oily product (1.0 g) was chromatographed on 50 g of silica gel
  3. washElution with 19:1 toluene-ethyl acetate

Sources & evidence

ORD record
ord-4168212c7f1b4e2d836af4d23c37cb49
Source dataset
uspto-grants-1988_11
Patent number
US04788214

Reaction notes

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