p-Toluenesulfonic acid monohydrate → HCID 90408509, compound

HRID 1855063Notes

Reaction equation

HRID 1855063 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14]2([CH2:22][OH:23])[CH2:21][CH2:20][C:17]3([O:19][CH2:18]3)[CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CCOC(C)=O>[O:1]([C:8]1[CH:9]=[C:10]([C:14]23[CH2:15][CH2:16][C:17]([CH2:18][OH:19])([CH2:20][CH2:21]2)[O:23][CH2:22]3)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 90408609HCID 90408609, compound

Product 1

HCID 90408509HCID 90408509, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (6-(3-phenoxyphenyl)-1-oxaspiro[2.5]octan-6-yl)methanol (55.9 mg, 0.180 mmol) in CH2Cl2 (2 mL) at 0° C. was added p-toluenesulfonic acid monohydrate (3.43 mg, 0.018 mmol). The solution was warmed to rt and stirred for 1 h. The reaction was then diluted with EtOAc, washed successively with sat'd aq NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 (0 to 100% EtOAc:hexanes) to afford the title compound (15 mg, 27% yield) as an oil. LCMS, [M+Na]+=333.0.

Workup

  1. washwashed successively with sat'd aq NaHCO3, water, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on SiO2 (0 to 100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f0582c6d5c2f43ffb184b651562eb9ca
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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