Triphenylphosphine → HCID 70157633, compound

HRID 1069240Notes

Reaction equation

HRID 1069240 reaction equation
[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([OH:24])=[C:19]([CH3:25])[CH:18]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.O[C@@H:27]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:28]([O:30][CH3:31])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1>[CH3:31][O:30][C:28](=[O:29])[C@H:27]([O:24][C:20]1[C:21]([CH3:23])=[CH:22][C:17]([C:9]2[C:10]3[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=3[C:2]([Br:1])=[C:3]3[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]3)=[CH:18][C:19]=1[CH3:25])[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 18430706HCID 18430706, compound

Product 1

HCID 70157633HCID 70157633, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenol (5.0 g, 12.1 mmol), (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (3.3 g, 18.3 mmol), and triphenylphosphine (4.8 g, 18.3 mmol) in anhydrous benzene (50 mL) at room temperature under nitrogen was added dropwise diethyl azodicarboxylate (2.6 mL, 18.3 mmol) over a period of 25 min. The reaction mixture was heated for 2 h, then stirred at room temperature for 3 days. The crude reaction mixture was adsorbed onto silica gel and chromatographed twice with petroleum ether:ethyl acetate (95:5) to yield the title compound as a white foamy solid (4.5 g, 65%): NMR (DMSO-d6): δ8.18 (d, 1H), 7.64 (ddd, 1H), 7.53-7.43 (m, 2H), 7.38-7.24 (m, 5H), 7.00 (s, 2H), 4.80 (t, 1H), 3.58 (s, 3H), 3.31 (m, 2H), 2.42 (s, 3H), 2.24 (s, 3H), 2.19 (s, 3H), 1.55 (s, 3H); MS(EI): [M+], 1 bromine isotope pattern, 572/574; Anal. Calc. for C32H29BrO3S: C, 67.01; H, 5.10; N, 0.00. Found: C, 66.33; H, 5.09; N, 0.09; Analytical HPLC indicates a major component (94.39%).

Workup

  1. temperatureThe reaction mixture was heated for 2 h
  2. customThe crude reaction mixture
  3. customchromatographed twice with petroleum ether:ethyl acetate (95:5)

Sources & evidence

ORD record
ord-d372d2f4145b48c8bfb149b1b40865dc
Source dataset
uspto-grants-2001_06
Patent number
US06251936B1

Reaction notes

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