Methanol → Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

HRID 399348

反応式

HRID 399348 の反応式
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].CO.[H][H]>CO.O1CCCC1.C(C1C=C(C(C)(C)C)C2OP([C-]3C=CC=C3)OC3C(C(C)(C)C)=CC(C(C)(C)C)=CC=3C=2C=1)(C)(C)C.[C-]1(P2OC3C(C(C)(C)C)=CC(C(C)(C)C)=CC=3C3C=C(C(C)(C)C)C=C(C(C)(C)C)C=3O2)C=CC=C1.[Fe+2]>[CH3:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9]

参加物

6

反応物 3

HCID 887MethanolHCID 69240Dimethyl itaconate2 回HCID 178418361HCID 178418361、化合物

生成物 1

HCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl ester収率 99.1%

試薬・触媒・溶媒 2

HCID 1317208751,1'-Bis[2,4,8,10-tetrakis(tert-butyl)-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]ferrocene触媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

A mixture of 33 mg (0.031 mmol) of the ferrocenyl bis(phosphonite) prepared in Example 1 and 12 mg (0.031 mmol) of bis(bicyclo[2.2.1]hepta-2,5-diene)rhodium(I) perchlorate in 2 mL of methanol/tetrahydrofuran (1:1) solution is stirred for two hours. Then, to the resultant solution of rhodium complex is added a solution of 490 mg (3.1 mmol) of dimethyl itaconate and 13 mL of methanol in a pressure reactor. The reactor is then pressurized to 1018 psi with hydrogen and the reaction is stirred at ambient temperature for 88 hours. 1H nmr analysis of the reaction mixtures shows a 100% conversion of dimethyl itaconate starting material to product. Workup of the reaction mixture gives 492 mg (99% yield) of desired dimethyl 2-methylsuccinate.

後処理

  1. stirringthe reaction is stirred at ambient temperature for 88 hours

出典と根拠

ORDレコード
ord-01ee56ea5f4542ab891ac9b67fc5cba5
出典データセット
uspto-grants-1998_10
特許番号
US05817850

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