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

HRID 1381751
Notes
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Reaction equation

HRID 1381751 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-55ab970a064045e8a2bed0029fb38b5b
Source dataset
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04803301

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes