CID 3920069 → HCID 67708349, compound

HRID 1779261Notes

Reaction equation

C=CC1C=CC=CC=1.[C:9]1([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]([O-:33])(=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:23]([OH:33])(=[O:32])[CH:24]=[CH:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1.[C:9]1([C:15]#[C:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 3920069CID 3920069

HCID 86750785HCID 86750785, compound

Product 1

HCID 67708349HCID 67708349, compound

Procedure

The ethyl bromocinnamate 9F is treated with diisobutylaluminum hydride (DIBAL) to give the alcohol, which is then coupled with an alkyl bromide to give the styrene ether 9G. This ether is then coupled with alkyne 9E, again using a palladium catalyst, to give the tolane styrene 1H. Alternatively, the alkyne can be coupled with the original cinnamate to give a tolane cinnamate. If desired, the ester group can be derivatized by sequential hydrolysis, conversion to an acid chloride, and reaction with an alkanol to give the tolane cinnamate 9I.

Sources & evidence

ORD record: ord-189087cc4c724fb38a3a8e1915bca413
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05626792

Reaction notes

Loading…