Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 54099982, compound

HRID 2231910Notes

Reaction equation

[C:1]1([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]3[CH2:13][CH2:14][CH:15](O)[O:16][C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([CH:25]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:22][CH2:23][CH3:24])=[O:21]>>[CH2:23]([O:22][C:20](=[O:21])[CH2:25][CH:15]1[CH2:14][CH2:13][C:12]2[CH:18]=[CH:19][C:9]([O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:10][C:11]=2[O:16]1)[CH3:24]

Participants

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

HCID 14329764HCID 14329764, compound

Product 1

HCID 54099982HCID 54099982, compoundYield 92.8%

Procedure

A 2.2 g sample of racemic-3,4-dihydro-7-(phenylmethoxy)-2h-1-benzopyran-2-ol was condensed with (carbethoxymethylene)triphenylphosphorane (3.2 g) using the procedure of Example 30. There was obtained 2.6 g (92.8%) of racemic-3,4-dihydro-7-(phenylmethoxy)-2H-1-benzopyran-2-acetic acid ethyl ester as a yellow oil, after column chromatographic purification. This material was hydrogenolyzed over 0.2 g of 10% palladium on carbon as described in Example 30. There was obtained 1.9 g of racemic-3,4-dihydro-7-hydroxy-2H-1-benzopyran-2-acetic acid ethyl ester as a pale-yellow oil.

Sources & evidence

ORD record: ord-c3bfca92db9d4b7da63b242f3d05cc06
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04785017

Reaction notes

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