Triphenylphosphine → HCID 12083247, compound

HRID 2417113Notes

Reaction equation

HRID 2417113 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH:2]=1.[CH2:22]([O:24][C:25](=[O:37])[C:26]([O:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)([CH3:28])[CH3:27])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1.C(OCC)(=O)C>[CH2:22]([O:24][C:25](=[O:37])[C:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([O:14][CH2:13][CH2:12][C:10]2[N:11]=[C:7]([C:3]3[CH:2]=[C:1]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:6]=[CH:5][CH:4]=3)[S:8][C:9]=2[CH3:15])=[CH:32][CH:31]=1)([CH3:28])[CH3:27])[CH3:23]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 181741Ethyl 2-(4-hydroxyphenoxy)-2-methylpropanoateHCID 5363146Diisopropyl azodicarboxylateHCID 22633483HCID 22633483, compound

Product 1

HCID 12083247HCID 12083247, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-biphenyl-3-yl-5-methyl-thiazol-4-yl)-ethanol (2.58 g, 8.73 mmol), 2-(4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester (1.96 g, 8.73 mmol), and triphenylphosphine (2.29 g, 8.73 mmol) in 90 mL tetrahydrofuran was added diisopropylazodicarboxylate (1.76 g, 8.73 mmol) dropwise over 30 min. After stirring 24 h, the solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated to an orange oil. Silica gel chromatography (100 g silica gel, 15% ethyl acetate/hexanes) afforded 470 mg (11% yield) of 2-{4-[2-(2-biphenyl-3-yl-5-methyl-thiazol-4-yl)-ethoxy]-phenoxy}-2-methyl-propionic acid ethyl ester as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.81 (d, 1H), 7.62 (d, 2H), 7.57 (d, 1H), 7.46-7.42 (m, 3H), 7.37-7.34 (m, 1H), 6.80-6.74 (m, 4H), 4.235 (t, 2H), 4.20 (q, 2H), 3.15 (t, 2H), 2.44 (s, 3H), 1.49 (s, 6H), 1.24 (t, 3H). MS EI+ (m/e) 502.1

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an orange oil

Sources & evidence

ORD record
ord-f35daf9e643f47ac8a496f4cfa78da81
Source dataset
uspto-grants-2004_11
Patent number
US06825222B2

Reaction notes

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