Ethyl Acetate → 3-hexadecylthio-2-(5-methyl-1H-tetrazol-1-yl)propanol

HRID 728459Notes

Reaction equation

HRID 728459 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([N:41]1[C:45]([CH3:46])=[N:44][N:43]=[N:42]1)[CH2:20][O:21]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>CO.O1CCCC1>[CH2:1]([S:17][CH2:18][CH:19]([N:41]1[C:45]([CH3:46])=[N:44][N:43]=[N:42]1)[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 198842301-hexadecylthio-2-(5-methyl-1H-tetrazol-1-yl)-3-triphenylmethoxypropane

Product 1

HCID 148349853-hexadecylthio-2-(5-methyl-1H-tetrazol-1-yl)propanolYield 81%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 2.90 g (4.5 mM) of 1-hexadecylthio-2-(5-methyl-1H-tetrazol-1-yl)-3-triphenylmethoxypropane and 170 mg (0.9 mM) of p-toluenesulfonic acid monohydrate in 60 ml of methanol-tetrahydrofuran (1:1) mixture is stirred at room temperature for overnight. The mixture was poured into ice-water containing 151 mg (1.8 mM) of sodium bicarbonate and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated. The residue is purified by column silica gel chromatography using toluene:ethyl acetate (4:1-1:1) mixture as an eluent and 1.46 g (81% yield) of the title compound Vi1 is obtained. mp. 77°-78° C.

Workup

  1. washThe ethyl acetate layer is washed with saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe residue is purified by column silica gel chromatography

Sources & evidence

ORD record
ord-539270e085ec4150a5c6aae3e3c66ec9
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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