Water → HCID 66936679, compound

HRID 1364007Notes

Reaction equation

HRID 1364007 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, compound

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 (28′) (290 mg, 0.97 mmol) in acetone (6 mL) was added H2O (catalytic amount) and p-toluenesulfonic acid (catalytic amount). The reaction mixture is stirred at room temperature overnight and then dried over anhydrous MgSO4. The solution is filtered through silica and the filtrate concentrated under reduced pressure. The resulting residue is purified over silica (isooctane/EtOAc, 7:3) to afford the desired product as a colorless oil which was characterized as follows:

Workup

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

Sources & evidence

ORD record
ord-7fb851c8e9e14b47a4d1bf3bae10889b
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

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