4-Hydroxybiphenyl → (2S)-2-(Biphenyl-4-yloxy)propanoic acid, ethyl ester

HRID 379964Notes

Reaction equation

HRID 379964 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C@@H:33]([CH3:35])[OH:34].[C:40]1([C:46]2[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCCC1>[C:40]1([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:45]=[CH:44][C:43]([O:34][C@@H:33]([CH3:35])[C:32]([O:37][CH2:38][CH3:39])=[O:36])=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 637513ethyl (2R)-2-hydroxypropanoateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 71354156(2S)-2-(Biphenyl-4-yloxy)propanoic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the method described in Example 1a) from diethylazodicarboxylate (6.74 ml), triphenylphosphine (13.11 g), (R)-(+)-ethyl lactate (5.67 ml) and 4-phenylphenol (8.51 g) in dry tetrahydrofuran (125 ml). The residue obtained after work-up was purified by column chromatography over silica eluting with isohexane:dichloromethane (2:3) to give the sub-title compound as an oil (11.3 g).

Workup

  1. customPrepared
  2. customThe residue obtained after work-up
  3. customwas purified by column chromatography over silica eluting with isohexane:dichloromethane (2:3)

Sources & evidence

ORD record
ord-bc0780f1be2d453ca71b560461bf9b78
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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