p-Toluenesulfonic acid monohydrate → 3-hexadecylthio-2-(5-methyl-2H-tetrazol-2-yl)propanol

HRID 728460Notes

Reaction equation

HRID 728460 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([N:41]1[N:45]=[N:44][C:43]([CH3:46])=[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.CC1N=NN(C(COC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)CO)N=1>CO.O1CCCC1>[CH2:1]([S:17][CH2:18][CH:19]([N:41]1[N:45]=[N:44][C:43]([CH3:46])=[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

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 148350992-(5-methyl-2H-tetrazol-2-yl)-3-triphenylmethoxypropanolHCID 198841961-hexadecylthio-2-(5-methyl-2H-tetrazol-2-yl)-3-triphenylmethoxypropane

Product 1

HCID 148349873-hexadecylthio-2-(5-methyl-2H-tetrazol-2-yl)propanol

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Using 10.2 g of crude 1-hexadecylthio-2-(5-methyl-2H-tetrazol-2-yl)-3-triphenylmethoxypropane 5h and 500 mg (2.6 mM) of p-toluene sulfonic acid monohydrate in 200 ml of methanol-tetrahydrofurane (1:1) mixture is converted to 3.17 g (49% from the compound 4h) of the title compound Vh1 by the same procedure as described in (81).

Sources & evidence

ORD record
ord-1fe82996e621479cb523335cf41ab9b6
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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