Benzene, [1-[(trimethylsilyl)oxy]ethenyl]- → 3-[[2-(Cyclopropylmethyl)phenyl]thio]-4-hydroxy-6-phenyl-2H-pyran-2-one

HRID 613126Notes

Reaction equation

HRID 613126 reaction equation
[C:1]1([C:7]([O:9][Si](C)(C)C)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:14]1([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24][CH:25]([C:29](O)=[O:30])[C:26](O)=[O:27])[CH2:16][CH2:15]1>>[CH:14]1([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[S:24][C:25]2[C:26](=[O:27])[O:9][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:29]=2[OH:30])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 117406Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-HCID 19596062[[2-(Cyclopropylmethyl)phenyl]thio]propandioic acid

Product 1

HCID 546812143-[[2-(Cyclopropylmethyl)phenyl]thio]-4-hydroxy-6-phenyl-2H-pyran-2-one

Procedure

The title compound was prepared by Method A using 1-phenyl-1-(trimethylsilyloxy)ethylene (0.990 mL, 4.83 mmol), and diethyl ester of [[2-(cyclopropylmethyl)phenyl]thio] propanedioic acid (1.00 g, 3.10 mmol) m.p. 165-167° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.25 (dd, 2H), 0.52 (dd, 2H), 1.21 (m, 1H), 2.50 (d, 2H), 6.87 (s, 1H), 6.92 (m, 1H), 7.05 (m, 2H), 7.32 (m, 1H), 7.56 (m, 3H), 7.86 (m, 2H).

Sources & evidence

ORD record
ord-0cfe4516b2354e728cc7ab55d82b1167
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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