Triphenylphosphine → HCID 22633852, compound

HRID 1369318Notes

Reaction equation

HRID 1369318 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:9]([Si:13](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:12])([CH3:11])[CH3:10].S(Cl)(C)(=O)=O.[N-:32]=[N+]=[N-].[Li+].[N-]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1C=CC=CC=1.CN(C=O)C>[Si:13]([CH:6]([OH:7])[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:32])([C:9]([CH3:12])([CH3:11])[CH3:10])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 6

HCID 11776TriphenylphosphineHCID 123741,6-HexanediolHCID 31297Methanesulfonyl chlorideHCID 33558AzideHCID 88163Lithium azideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 22633852HCID 22633852, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolvent

Procedure

1,6-Hexanediol is monosilylated with tert-butylchloro-diphenylsilane (1 equivalent) in dry pyridine. It is then mesylated with mesyl chloride in pyridine and subsequently treated with lithium azide in DMF solvent. The resulting azide derivative is reduced with triphenyl phosphine to give the title compound.

Sources & evidence

ORD record
ord-8e10a23d5aa741b4816360a43c6abbd8
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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