Triethylamine → HCID 59712110, compound

HRID 2222219Notes

Reaction equation

HRID 2222219 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][OH:16].CCN(CC)CC.[O:24](S(C1C=CC(C)=CC=1)(=O)=O)[S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=O)=[O:26]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:32][C:31]1[CH:33]=[CH:34][C:28]([S:25]([O:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)(=[O:26])=[O:24])=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 11345082(2-{[(Oxan-2-yl)oxy]methyl}phenyl)methanol

Product 1

HCID 59712110HCID 59712110, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of {2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl}methanol (5.52 g, 24.84 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. and treated with Et3N (6.92 ml, 49.68 mmol) followed by the addition of Ts2O (8.9 g, 27.33 mmol). The reaction stirred at 0° C. for 3.5 hours. The mixture was diluted with sat. NH4Cl and extracted with CH2Cl12 (2×). The combined organic solutions were washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%) to give a light brown oil (7.36 g).

Workup

  1. extractionextracted with CH2Cl12 (2×)
  2. washThe combined organic solutions were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%)

Sources & evidence

ORD record
ord-676f11735f084b89b3a25bd26dfc06c5
Source dataset
uspto-grants-2008_05
Patent number
US07371754B2

Reaction notes

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