Sodium Hydroxide → HCID 69797416, compound

HRID 1268253Notes

Reaction equation

C([O:3][C:4](=[O:34])[C@@H:5]([O:31][CH2:32][CH3:33])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](/[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)\[CH3:17])=[CH:9][CH:8]=1)C.[OH-].[Na+]>>[Br:30][C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:20]=[CH:19][C:18](/[C:16](/[CH3:17])=[CH:15]/[CH2:14][O:13][C:10]3[CH:11]=[CH:12][C:7]([CH2:6][C@H:5]([O:31][CH2:32][CH3:33])[C:4]([OH:34])=[O:3])=[CH:8][CH:9]=3)=[CH:23][CH:22]=2)=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69797104HCID 69797104, compound2×

Product 1

HCID 69797416HCID 69797416, compound

Procedure

The title compound was prepared from (E)-(S)-3-{4-[3-(4′-bromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester (example 3) (0.150 g, 0.29 mmol) and sodium hydroxide (1M, 0.45 ml, 0.45 mmol) by a procedure analogous to that described in example 2 yielding 0.180 g (34%) of (E)-(S)-3-{4-[3-(4′-bromo-biphenyl-4-yl)-but-2-enyloxy]-phenyl}-2-ethoxy-propionic acid ethyl ester.

Sources & evidence

ORD record: ord-a2d797f02433475f8426d9148535953b
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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