Hydrochloric Acid → (αS)-3,4-Dichloro-α-ethylbenzenemethanol
Reaction equation
CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.C(N(CC)C1C=CC=CC=1)C.B.[Cl:34][C:35]1[CH:36]=[C:37]([C:42](=[O:45])[CH2:43][CH3:44])[CH:38]=[CH:39][C:40]=1[Cl:41].Cl>CO.CC(OC)(C)C>[Cl:34][C:35]1[CH:36]=[C:37]([C@@H:42]([OH:45])[CH2:43][CH3:44])[CH:38]=[CH:39][C:40]=1[Cl:41]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
A 250 mL round-bottom flask was charged with MTBE (35 mL), a solution of (R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole (2.51 mL, 2.51 mmol) and borane diethylaniline (4.45 mL, 25.1 mmol) at RT then heated to 40° C. A MTBE (20 mL) solution of 156 (6.00 g, 25.1 mmol) was added dropwise and the reaction was stirred at 40° C. for 3 h. The reaction was cooled to RT and MeOH (5 mL) was then added slowly, followed by 1M HCl and the reaction was stirred for 18 h. The water was removed and the remaining organic phase dried (Na2SO4), filtered and concentrated to get a light gray oil. The crude product was purified by SiO2 chromatography (SNAP 100) eluting with EtOAc/hexane (1:3) to afford 3.45 g (66%) of (S)-1-(3,4-dichlorophenyl)propan-1-ol (158) as a clear oil.
Workup
- temperatureThe reaction was cooled to RT
- stirringthe reaction was stirred for 18 h
- customThe water was removed
- dry with materialthe remaining organic phase dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customto get a light gray oil
- customThe crude product was purified by SiO2 chromatography (SNAP 100)
- washeluting with EtOAc/hexane (1:3)
Sources & evidence
- ORD record
- ord-67d66dd55314418ca516d09110611aff
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133187B2
Reaction notes
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