1,8-Diazabicyclo(5.4.0)undec-7-ene → 2Z-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-acrylic acid ethyl ester

HRID 479221Notes

Reaction equation

HRID 479221 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:26])=[C:13]([CH2:15][O:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19](C)[CH:18]=3)[N:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[CH2:28]([O:30][CH:31]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:29].[CH2:56]1CCN2C(=NCCC2)CC1>>[CH2:35]([O:34][C:32](=[O:33])/[C:31](/[O:30][CH2:28][CH3:29])=[CH:21]/[C:20]1[CH:23]=[CH:24][C:17]([O:16][CH2:15][C:13]2[N:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=3)[O:11][C:12]=2[CH3:26])=[CH:18][C:19]=1[CH3:56])[CH3:36]

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)2×HCID 180036004-[2-(4-Isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-benzaldehyde

Product 1

HCID 695568762Z-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-acrylic acid ethyl ester

Procedure

In analogy to the procedure described in example 120 f], 4-hydroxy-2-methyl-benzaldehyde (for the preparation of 4-hydroxy-2-methyl-benzaldehyde see: H. H. Hodgson, T. A. Jenkinson, J. Chem. Soc. 1929, 469, 1639-1641) was reacted with 4-chloromethyl-2-(4-isopropyl-phenyl)-5-methyl-oxazole (prepared from 4-isopropyl-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 21 a] and b]) in the presence of potassium carbonate to yield 4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-benzaldehyde. 4-[2-(4-Isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-benzaldehyde was reacted with (ethoxy-ethoxy-carbonyl-methyl)-triphenyl-phosphonium chloride [for the preparation of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride see: K. K. Bach, H. R. El-Seedi, H. M. Jensen, H. B. Nielsen, I. Thomson, K. B. G. Torssell, Tetrahedron 1994, 50, 7543-7556] in the presence of DBU in analogy to the procedure described in example 120 c] to give 2Z-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-acrylic acid ethyl ester, which was further saponified in analogy to the procedure described in example 120 f] to yield 2Z-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-acrylic acid as light green solid.

Sources & evidence

ORD record
ord-54bb59ea67494eeaa18df75bbb8c4a4c
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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