Acetic Anhydride → HCID 86735848, compound

HRID 866705Notes

Reaction equation

OC(CCCCCC)/C=C/[CH:5]1[CH:9]([CH:10]([CH3:12])[CH3:11])[CH2:8][C:7](=[O:13])[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]C(O)=O.[C:30]([O:34][C:35](=[O:38])[CH2:36][CH3:37])(=O)[CH2:31][CH3:32].C([O:42][C:43](=[O:45])C)(=O)C>>[C:35]([O:34][CH:30]([CH2:10][CH2:9][CH2:5][CH2:6][CH2:7][CH3:8])[CH:31]=[CH:32][CH:5]1[CH:9]([CH:10]([CH3:11])[CH3:12])[CH2:8][C:7](=[O:13])[CH:6]1[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:43]([OH:42])=[O:45])(=[O:38])[CH2:36][CH3:37]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 31263Propionic anhydride

HCID 21312669HCID 21312669, compound

Product 1

HCID 86735848HCID 86735848, compound

Procedure

In the same manner but using the appropriate choice of compound of formula I (R1 =H) and lower alkanoic anhydride, then other compounds of formula I (R= lower alkanoyl and if R2 is CH2OR3 then R3 is lower alkanoyl) are prepared. For example the choice of trans-8-[2-(3-hydroxy-1-nonenyl)-3-isopropyl-5-oxocyclopentyl]octanoic acid (Example 144) and propionic anhydride instead of the compound of formula I and acetic anhydride noted in the procedure of this Example, give trans-8-[(2-(3-propionoxy-1-nonenyl)-3-isopropyl-5-oxocyclopentyl]octanoic acid. Similarly, ethyl trans-8-[2-3-hydroxy-1-heptenyl)-5-oxocyclopentyl]-6-octynoate (see Example 161) and butyric anhydride gives ethyl trans-8-[2-(3-butyryloxy-1-heptenyl)-5-oxocyclopentyl]-6-octynate.

Sources & evidence

ORD record: ord-99be7c409d17486c85e142516e93e787
Source dataset: uspto-grants-1978_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04100343

Reaction notes

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