Ethanol → Methyl 4-(Diethylaminosulfonyl)benzenepropanoate

HRID 54978ノート

反応式

HRID 54978 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:16]([O-:20])(=[O:19])[CH:17]=C.[CH2:21](O)C>[Pd]>[CH2:14]([N:11]([CH2:12][CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][CH2:17][C:16]([O:20][CH3:21])=[O:19])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH3:15]

参加物

4

反応物 2

HCID 702EthanolHCID 86748378HCID 86748378、化合物

生成物 1

HCID 19957168Methyl 4-(Diethylaminosulfonyl)benzenepropanoate

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

To 14.5 g of N,N-diethyl-4-bromobenzenesulfonamide (50 mmol) (prepared by reaction of 4-bromobenzenesulfonyl chloride with diethylamine) was added 13.8 g of tetrabutylammonium chloride (50 mmol), 10.3 g of NaHCO3 (124 mmol), 266 mg of palladium (II) acetate (1.07 mmol) and 100 mL of DMF in the order given. To this suspension was added 8.8 ml of methyl acrylate (98 mmol) and the reaction was stirred 1 hour at 80°. The reaction was cooled, 500 mL of water and 900 mL of ether were added, the layers were separated and the ether layer was filtered to remove Pd (0) and combined with 2 further ether washes of the aqueous phase. The combined ether solutions were dried over MgSO4, filtered, stripped and recrystallized from methanol/ether to yield 9.4 g of methyl 4-(diethylaminosulfonyl)benzene-2-propenoate. Six grams of the propenoate was reduced in ethanol at 3.5 atm over 10% Pd on carbon in a Parr Shaker to produce 5.9 g of product as a yellow oil. It was used in that form in Example 269.

出典と根拠

ORDレコード
ord-81c566c9c9bf4c40b78c4201e68eceae
出典データセット
uspto-grants-1997_04
特許番号
US05624922

反応ノート

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