Propylene Glycol → (S)-1-(tert-Butoxy)-3-cyclohexyl-propan-2-ol

HRID 1532869Notes

Reaction equation

HRID 1532869 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].[C:6](NC(=O)C(Cl)(Cl)Cl)([CH3:9])([CH3:8])[CH3:7].C([O-])(O)=O.[Na+].[CH2:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>[B]>[C:6]([O:5][CH2:1][C@@H:2]([OH:4])[CH2:3][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)([CH3:7])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 8078CyclohexaneHCID 304045N-tert-butyl-2,2,2-trichloroacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 59949160(S)-1-(tert-Butoxy)-3-cyclohexyl-propan-2-ol

Reagents, catalysts & solvents 1

HCID 5462311BoronCatalyst

Procedure

(S)-1-(tert-Butoxy)-3-cyclohexyl-propan-2-ol was prepared according to the procedure described by Alan Armstrong et al., Tetrahedron Letters 1988, 29: 2483-2486. Three drops of boron trifuoride etherate were added to a solution of (S)-3-cylcolhexyl 1,2-propanediol (540 mg, 3.4 mmol) and tert-butyl 2,2,2-trichloroacetamide (670 μL, 3.8 mmol) in cyclohexane (7 mL) at ambient temperature. After stirring for 21 hours, a saturated solution of NaHCO3 was added to the reaction mixture and the mixture was extracted with EtOAc (2×). The EtOAc phases were combined, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes, 1:10) to afford a clear oil (235 mg, 32%). 1H NMR (CDCl3, 300 MHz) δ0.79-1.01 (m, 2H), 1.12-1.53 (m, 6H), 1.20 (s, 9H) 1.58-1.84 (m, 5H), 3.12 (dd, J=9, 9 Hz, 1H), 3.35 (dd, J=3, 9 Hz, 1H), 3.81 (m, 1H); MS (CI/NH3) m/z: (M+H)+ 215.

Workup

  1. extractionthe mixture was extracted with EtOAc (2×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed (silica gel; EtOAc/hexanes, 1:10)

Sources & evidence

ORD record
ord-2f7cd15ccb8f4553a7b9c845e10a36d0
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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