HCID 57706290, compound → HCID 22926843, compound

HRID 1662363Notes

Reaction equation

HRID 1662363 reaction equation
OC1C=C(C[C@@H](C)C(OC)=O)C=CC=1.OC1C=C(C[C@H](C)C(OC)=O)C=CC=1.[OH:29][C:30]1[CH:31]=[C:32]([CH2:36][C@@H:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:33]=[CH:34][CH:35]=1.OC1C=C(C[C@H](C)C(OCC)=O)C=CC=1>>[OH:29][C:30]1[CH:31]=[C:32]([CH2:36][CH:37]([CH3:43])[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 4

HCID 57706290HCID 57706290, compoundHCID 57707095Benzenepropanoic acid, 3-hydroxy-α-methyl-, ethyl ester, (αR)-HCID 67428994HCID 67428994, compoundHCID 67430489HCID 67430489, compound

Product 1

HCID 22926843HCID 22926843, compound

Procedure

Methyl (2R)-3-(3-hydroxyphenyl)-2-methylpropanoate (62) and methyl (2S)-3-(3-hydroxyphenyl)-2-methylpropanoate (63). Racemic ethyl 3-(3-hydroxyphenyl)-2-methylpropanoate 62.C (0.40 g) was separated by ChiralPak OJ-H column, eluted with 10% isopropanol in hexane to give the separated enantiomers; (R)-ethyl 3-(3-hydroxyphenyl)-2-methylpropanoate and (S)-ethyl 3-(3-hydroxyphenyl)-2-methylpropanoate 62 and 63. MS ESI (pos.) m/e: 209.1 (M+H)+.

Workup

  1. customRacemic ethyl 3-(3-hydroxyphenyl)-2-methylpropanoate 62.C (0.40 g) was separated by ChiralPak OJ-H column
  2. washeluted with 10% isopropanol in hexane
  3. customto give the separated enantiomers

Sources & evidence

ORD record
ord-c9f5aa1d0f784c08a58d022781768ff4
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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