p-Toluenesulfonic acid monohydrate → 3-Hexadecylthio-2-(3-isoxazolyloxy)propanol

HRID 728470Notes

Reaction equation

HRID 728470 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([O:41][C:42]1[CH:46]=[CH:45][O:44][N:43]=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(SCC(N1C(C)=NN=N1)CO)CCCCCCCCCCCCCCC>CO.O1CCCC1>[CH2:1]([S:17][CH2:18][CH:19]([O:41][C:42]1[CH:46]=[CH:45][O:44][N:43]=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 148349853-hexadecylthio-2-(5-methyl-1H-tetrazol-1-yl)propanolHCID 198842281-Hexadecylthio-2-(3-isoxazolyloxy)-3-triphenylmethoxypropane

Product 1

HCID 148349913-Hexadecylthio-2-(3-isoxazolyloxy)propanolYield 94%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of 7.30 g (11 mM) of 1-hexadecylthio-2-(3-isoxazolyloxy)-3-triphenylmethoxypropane 5j and 433 mg (2.3 mM) of p-toluenesulfonic acid monohydrate in 150 ml of methanol-tetrahydrofuran (1:1) mixture by the same procedure as described in (81) to give 4.25 g of the titled compound Vj1 (94% yield).

Sources & evidence

ORD record
ord-c835450f993c4681acdb33f14172a6f8
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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