Triphenylphosphine → HCID 22633852, compound

HRID 2417294Notes

Reaction equation

HRID 2417294 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-30b0a78b3c134b06bc281efc39f18039
Source dataset
uspto-grants-2004_11
Patent number
US06825331B2

Reaction notes

Loading…