Tributylphosphine → Ethyl 3-(4-[[3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methoxy]-2-ethylphenyl)propanoate

HRID 2177280Notes

Reaction equation

HRID 2177280 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][OH:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[S:4][N:3]=1.[CH2:16]([C:18]1[CH:23]=[C:22](O)[CH:21]=[CH:20][C:19]=1[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:17].C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.P(CCCC)(CCCC)CCCC>>[Cl:1][C:2]1[C:6]([CH2:7][O:8][C:22]2[CH:21]=[CH:20][C:19]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:18]([CH2:16][CH3:17])[CH:23]=2)=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[S:4][N:3]=1

Participants

5

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 45095457Ethyl 3-(2-ethyl-4-hydroxyphenyl)propanoateHCID 90418566[3-Chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol

Product 1

HCID 90418453Ethyl 3-(4-[[3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methoxy]-2-ethylphenyl)propanoate

Conditions

Temperature
60 °C

Procedure

Into a 8-mL vial purged and maintained with an inert atmosphere of nitrogen, was placed [3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methanol (80 mg, 0.33 mmol, 1.00 equiv), ethyl 3-(2-ethyl-4-hydroxyphenyl)propanoate (89.17 mg, 0.40 mmol, 1.20 equiv), ADDP (210.87 mg, 0.84 mmol, 2.52 equiv), n-Bu3P (101.42 mg), Tol (1.5 mL). The resulting solution was stirred overnight at 60° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6). This resulted in 123 mg (83%) of ethyl 3-(4-[[3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methoxy]-2-ethylphenyl)propanoate as colorless oil. Mass spectrum (ESI, m/z): Calcd. for C21H21FO5, 444.1 (M+H). found 444.1.

Workup

  1. customInto a 8-mL vial purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 123 mg (83%) of ethyl 3-(4-[[3-chloro-5-(2-methylphenyl)-1,2-thiazol-4-yl]methoxy]-2-ethylphenyl)propanoate as colorless oil

Sources & evidence

ORD record
ord-954e75e0d0af4c27931936117c7cb10a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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