Benzaldehyde → HCID 13573803、化合物

HRID 280377

反応式

HRID 280377 の反応式
[OH:1][CH2:2][CH:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:10]1([C@@H:9]2[N:7]3[C:6](=[O:8])[CH2:5][CH2:4][CH:3]3[CH2:2][O:1]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 240BenzaldehydeHCID 1140TolueneHCID 5583595-(Hydroxymethyl)pyrrolidin-2-one

生成物 1

HCID 13573803HCID 13573803、化合物収率 86%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 962Water溶媒

実験手順

A mixture of 5-hydroxymethyl-2-pyrrolidone (85.0 g), benzaldehyde (98.0 g), p-toluenesulfonic acid (1.6 g) and toluene (500 ml) was heated to reflux using a Dean-Stark water separator and an oil bath, with vigorous stirring. After nine hours, the collection of water stopped and the cooled reaction mixture was washed with 5% sodium bicarbonate solution (2×50 ml), saturated sodium bisulfide solution (4×50 ml), water (2×50 ml) and brine (1×50 ml). The toluene solution was dried over andydrous magnesium sulfate and the solvent removed on a rotary evaporator. The residue obtained was distilled, 145°-150° C./0.1 mm Hg to give the title compound as an oil (129.0 g). [α]D =+269.6° (chloroform; c=1). TLC single spot at Rf =0.5 (silica gel, ethyl acetae-hexane; 4:1 UV and iodine).

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. customthe collection of water
  4. customthe cooled reaction mixture
  5. washwas washed with 5% sodium bicarbonate solution (2×50 ml), saturated sodium bisulfide solution (4×50 ml), water (2×50 ml) and brine (1×50 ml)
  6. dry with materialThe toluene solution was dried over andydrous magnesium sulfate
  7. customthe solvent removed on a rotary evaporator
  8. customThe residue obtained
  9. distillationwas distilled, 145°-150° C./0.1 mm Hg

出典と根拠

ORDレコード
ord-a737217631a3430981672bf8baa63b2d
出典データセット
uspto-grants-1986_05
特許番号
US04588819

関連ノート

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