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Triphenylphosphine → tert-butyl (2R)-(+)-2-(4'-(2",4"-dinitrophenoxy)phenoxy]propionate

HRID 1381751
ノート
印刷プレビュー

反応式

HRID 1381751 の反応式
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[N+:11]([C:14]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1)([O-:13])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[N+:11]([C:14]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([O:3][C@H:2]([CH3:4])[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:19][CH:18]=1)([O-:13])=[O:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 129406274-(2,4-Dinitrophenoxy)phenolHCID 129438461,1-Dimethylethyl (2S)-2-hydroxypropanoate

生成物 1

HCID 53785290tert-butyl (2R)-(+)-2-(4'-(2",4"-dinitrophenoxy)phenoxy]propionate収率 52.4%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a stirred solution of known tert-butyl L-(+)-lactate (1.00 g), 4-(2',4'-dinitrophenoxy)phenol (2.08 g) and triphenylphosphine (1.98 g) in dry tetrahydrofuran (58 ml) on an ice bath, diethylazodicarboxylate (1.18 ml) was added dropwise. After the addition, the ice bath was removed and the mixture was further stirred at room temperature for 19 hours. The reaction mixture was evaporated with a rotary evaporator. The residue thus obtained was purified by silica gel chromatography [silica gel 344 g, eluant:ethyl acetate-hexane (1:5)] to give tert-butyl (2R)-(+)-2-(4'-(2",4"-dinitrophenoxy)phenoxy]propionate (1.45 g). Since the product was decomosed even by high vacuum distillation, the viscous oily substance of the product thus obtained was left to stand at room temperature under high vacuum (0.25 Torr) for 2 hours, and then its physical data thereon were measured.

後処理

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction mixture was evaporated with a rotary evaporator
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography [silica gel 344 g, eluant:ethyl acetate-hexane (1:5)]

出典と根拠

ORDレコード
ord-55ab970a064045e8a2bed0029fb38b5b
出典データセット
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04803301

反応ノート

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