Tetrahydrofuran → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

HRID 1662372Notes

Reaction equation

HRID 1662372 reaction equation
CC1(C)CCC[C@H]1[C:7]1[CH:8]=[C:9](C=[CH:15][C:16]=1O)[C:10]([O:12][CH3:13])=[O:11].[CH3:19][C:20]1(C)CCC[C@@H]1C1C=C(C=CC=1O)C(OC)=O.CC1(C)C(C2C=C(C=CC=2O)C(OC)=O)=CCC1.[CH2:55]1[CH2:59][O:58][CH2:57][CH2:56]1>>[CH:7]1([CH:8]([C:55]2[CH:59]=[CH:20][CH:19]=[C:57]([OH:58])[CH:56]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 53376385(R)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoateHCID 53376485Methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-hydroxybenzoateHCID 57706328(S)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate

Product 1

HCID 57706598Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoateYield 99%

Procedure

(R)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate (66.6AA) or (S)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate (66.6AB). A mixture of Rh(COD)2BF4 (Stern Chemical, 35138-22-8, 137.2 mg, 0.338 mmol) and (R)-1-[(S)-2-(R)-(ditertbutylphosphino)ferrocenyl]ethyl-bis-(3,5-bistrifluoromethylphenyl)phosphine (Solvias, SL-J210-1, 302 mg, 0.3718 mmol) was stirred in THF (300 mL) under N2 for 60 minutes and a dark red solution formed. To the resulting solution was added methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-hydroxybenzoate 66.6H (41.64 g, 168.98 mmol) and TEA (10 mol %, 2.35 mL, 16.9 mmol). The resulting solution was filled with H2 (200 psi) three times and stirred at room temperature/200 psi for 2 hours. The reaction mixture was then passed through a short plug of silica gel, eluting with 1:1 hexane/EtOAc, followed by concentration afforded the desired product as a white solid (98.9A % conversion, 99% yield (41.6 g), 99% ee).

Workup

  1. customa dark red solution formed
  2. additionThe resulting solution was filled with H2 (200 psi) three times
  3. washeluting with 1:1 hexane/EtOAc
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-4331f2dd55bc4dc58a8415e31d7b5f3c
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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