Water → HCID 66936679, compound

HRID 1364005Notes

Reaction equation

HRID 1364005 reaction equation
[O:1]1[C:5]2([CH2:21][CH2:20][CH2:19][C:7]3([CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16])[CH2:8]3)[CH2:6]2)OCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[OH:17][C:15]([CH3:18])([CH3:16])[CH2:14][CH2:13][CH2:12][CH:9]1[CH2:10][CH2:11][C:7]2([CH2:19][CH2:20][CH2:21][C:5](=[O:1])[CH2:6]2)[CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 66936811HCID 66936811, compound

Product 1

HCID 66936679HCID 66936679, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-(1,4-dioxa-dispiro[4.1.4.3]tetradec-9-yl)-2-methyl-pentan-2-ol (18) (420 mg, 1.42 mmol) in acetone (9 mL) was added H2O (catalytic amount) and p-toluenesulfonic acid (catalytic amount). The reaction mixture was stirred at room temperature overnight and then dried over anhydrous MgSO4. The solution was filtered through silica and the filtrate concentrated under reduced pressure. The resulting residue was purified over silica (isooctane/EtOAc, 7:3) to afford 312 mg (86% yield) of the desired ketone isomer as a colorless oil which was characterized as follows:

Workup

  1. dry with materialdried over anhydrous MgSO4
  2. filtrationThe solution was filtered through silica
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe resulting residue was purified over silica (isooctane/EtOAc, 7:3)

Sources & evidence

ORD record
ord-022b7551437f47cc8b79ac9fd2627076
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

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