Ammonium Chloride → Benzyl 3-hydroxy-3-methylcyclobutanecarboxylate

HRID 1049313Notes

Reaction equation

HRID 1049313 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.[NH4+].[Cl-]>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

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 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

A −78° C. solution of benzyl 3-oxocyclobutanecarboxylate (11.05 g, 54.1 mmol) in THF (155 mL) was treated drop-wise with methyl magnesium bromide (3M in Et2O, 27.1 mL, 81 mmol) and the mixture stirred at −78° C. for 30 min. Saturated NH4Cl was added, the mixture extracted with EtOAc (2×) and the combined organic extracts were dried, evaporated and purified via silica gel chromatography (acetone/Hex) to afford benzyl 3-hydroxy-3-methylcyclobutanecarboxylate (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. extractionthe mixture extracted with EtOAc (2×)
  2. customthe combined organic extracts were dried
  3. customevaporated
  4. custompurified via silica gel chromatography (acetone/Hex)

Sources & evidence

ORD record
ord-6c6e2c11feff425da343918b1c4a4203
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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