4-Chlorophenol → HCID 14390986, compound

HRID 1381748Notes

Reaction equation

HRID 1381748 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 10953655tert-butyl (2R)-2-hydroxypropanoate

Product 1

HCID 14390986HCID 14390986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of known tert-butyl D-(-)-lactate (160 mg), 4-chlorophenol (108 μl) and triphenylphosphine (287 mg) in dry tetrahydrofuran (6 ml) on an ice bath, diethylazodicarboxylate (173 μl) was added dropwise over about 5 minutes. After the addition, the ice bath was removed and the mixture was further stirred at room temperature for 3 hours. The reaction mixture was then evaporated with a rotary evaporator (water bath temperature 25° C.). The residue thus obtained was purified by silica gel chromatography [silica gel 30 g, eluant:ethyl acetate-hexane (1:10)] to give tert-butyl (2S)-(-)-2-(4'-chlorophenoxy)-propionate (173 mg).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. customThe reaction mixture was then evaporated with a rotary evaporator (water bath temperature 25° C.)
  4. customThe residue thus obtained
  5. customwas purified by silica gel chromatography [silica gel 30 g, eluant:ethyl acetate-hexane (1:10)]

Sources & evidence

ORD record
ord-98a8a3734192407cb813d2de668a695f
Source dataset
uspto-grants-1989_02
Patent number
US04803301

Reaction notes

Loading…