4-Chlorophenol → tert-butyl (2R)-(+)-2-(4'-chlorophenoxy)propionate

HRID 1381750Notes

Reaction equation

HRID 1381750 reaction equation
[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])(=[O:5])[C@H:2]([CH3:4])[OH:3].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:3][C@H:2]([CH3:4])[C:1]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 129438461,1-Dimethylethyl (2S)-2-hydroxypropanoate

Product 1

HCID 54123615tert-butyl (2R)-(+)-2-(4'-chlorophenoxy)propionate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of known tert-butyl L-(+)-lactate (217 mg), 4-chlorophenol (219 μl) and triphenylphosphine (584 mg) in dry tetrahydrofuran (8 ml) on an ice bath, diethylazodicarboxylate (350 μl) was added dropwise over about 10 minutes. After the addition, the ice bath was removed and the mixture was further stirred at room temperatures for 24 hours. The reaction mixture was evaporated with a rotary evaporator (water bath temperaure 38° C.). The residue thus obtained was purified by silica gel chromatography [silica gel 50 g, eluant:ethyl acetate-hexane (1:10)] to give tert-butyl (2R)-(+)-2-(4'-chlorophenoxy)propionate (256 mg).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction mixture was evaporated with a rotary evaporator (water bath temperaure 38° C.)
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography [silica gel 50 g, eluant:ethyl acetate-hexane (1:10)]

Sources & evidence

ORD record
ord-21fea5f75c0c4e4d82e28ea2824e46ee
Source dataset
uspto-grants-1989_02
Patent number
US04803301

Reaction notes

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