Lithium borohydride → trans-(2-(3-Chloro-2-methylphenyl)cyclopropyl)methanol

HRID 2175313Notes

Reaction equation

HRID 2175313 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[C:11](OC)=[O:12])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70981958trans-Methyl 2-(3-chloro-2-methylphenyl)cyclopropanecarboxylate

Product 1

HCID 90006928trans-(2-(3-Chloro-2-methylphenyl)cyclopropyl)methanolYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-methyl 2-(3-chloro-2-methylphenyl)cyclopropanecarboxylate (0.042, 0.187 mmol) in THF (2.0 mL) was added 2.0 M lithium borohydride (0.467 ml, 0.935 mmol) dropwise at room temperature. The reaction was stirred at room temperature for 3 d. The mixture was partitioned between EtOAc and 1 N HCl. The organic layer separated, and the aqueous phase was extracted with EtOAc. The combined organic layer was dried (MgSO4) and concentrated to afford the title compound (23 mg, 63% yield) as pale-yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (d, J=8.0 Hz, 1H), 7.04 (t, J=7.7 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 3.86-3.65 (m, 2H), 2.53-2.45 (m, 3H), 1.90-1.82 (m, 1H), 1.39 (d, J=5.2 Hz, 1H), 0.97-0.90 (m, 2H).

Workup

  1. customThe mixture was partitioned between EtOAc and 1 N HCl
  2. customThe organic layer separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0c163f56757f4099b18760b7fcdb75a6
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…