Phenol → 2-Decylthio-3-hydroxynorbornane

HRID 366918

Reaction equation

HRID 366918 reaction equation
CN(P(=NP(=O)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C)C.C1(O)C=CC=CC=1.[CH2:43]([SH:53])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52].[O:54]1[CH:60]2[CH:55]1[CH:56]1[CH2:61][CH:59]2[CH2:58][CH2:57]1>P(N(C)C)(N(C)C)N(C)C>[CH2:43]([S:53][CH:60]1[CH:55]([OH:54])[CH:56]2[CH2:61][CH:59]1[CH2:58][CH2:57]2)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

6

Reactant 4

HCID 996PhenolHCID 89171-DecanethiolHCID 18463exo-2,3-EpoxynorbornaneHCID 9829709Phosphoric triamide, tris[tris(dimethylamino)phosphoranylidene]-

Product 1

HCID 102214812-Decylthio-3-hydroxynorbornaneYield 95%

Reagents, catalysts & solvents 1

HCID 15355Hexamethylphosphorous triamideSolvent

Procedure

A reaction was conducted as described in Example 1 except that tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide was replaced with the same molar amount of a partially hydrated tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide, [(Me2N)3P=N]3P=O.0.29H2O, phenol was replaced with the same molar amount of decanethiol and PGE was replaced with 2,3-epoxynorbornane. Desired 2-decylthio-3-hydroxynorbornane was formed in an analytical yield of 95% and isolated in a yield of 90%.

Sources & evidence

ORD record
ord-307063b2ab434fabb0a5c3ee1233789e
Source dataset
uspto-grants-2000_10
Patent number
US06130346

Linked notes

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