Benzyl 3-oxocyclobutane-1-carboxylate → Benzyl 3-hydroxy-3-methylcyclobutanecarboxylate

HRID 715129Notes

Reaction equation

HRID 715129 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.[CH3:16][Mg]Br>C1COCC1>[OH:1][C:2]1([CH3:16])[CH2:5][CH:4]([C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:7])[CH2:3]1

Participants

4

Reactant 2

HCID 15830669Benzyl 3-oxocyclobutane-1-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 58254352Benzyl 3-hydroxy-3-methylcyclobutanecarboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Treat a −78° C. solution of benzyl 3-oxocyclobutanecarboxylate (11.05 g, 54.1 mmol) in THF (155 mL) drop-wise with methyl magnesium bromide (3M in diethyl ether, 27.1 mL, 81 mmol) and stir at −78° C. for 0.5 h. Add satd. NH4Cl, extract with EtOAc (2×), dry the combined organics, evaporate and purify via silica gel chromatography (acetone/hexanes) to afford the title compound (5.589 g, 47%) as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.36-7.29 (m, 5H); 5.08 (m, 3H); 2.75-2.66 (m, 1H); 2.13-2.12 (m, 4H); 1.21 (s, 3H); MS (ESI) m/z: 243.1 (M+Na+).

Workup

  1. additionAdd satd
  2. extractionNH4Cl, extract with EtOAc (2×)
  3. customdry the combined organics,
  4. customevaporate
  5. custompurify via silica gel chromatography (acetone/hexanes)

Sources & evidence

ORD record
ord-9b254e0a7e1340989247374bef4e6e8b
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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