Diethyl Ether → HCID 53956501, compound

HRID 2231903Notes

Reaction equation

HRID 2231903 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-389e7176b955497fb92f76e632a30626
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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