HCID 178527012, compound → HCID 22400797, compound

HRID 260995Notes

Reaction equation

HRID 260995 reaction equation
[PH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[O:23]S(C(F)(F)F)(=O)=O)=O>C(N(CC)CC)C>[PH2:1][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[OH:23]

Participants

3

Reactant 1

HCID 178527012HCID 178527012, compound

Product 1

HCID 22400797HCID 22400797, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

More specifically, following Tetrahedron Letters, 31, 6321-6324 (1990), trifluoromethanesulfonic anhydride (4) is reacted with 1,1-bi-2-naphthol (3) to form 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl (5). This compound (5) is reacted with phosphine oxide (6) in the presence of a palladium catalyst to form 2-phosphinyl-2'-trifluoromethanesulfonyloxy-1,1'-binaphthyl (7). Compound (7) is then reduced in the presence of triethylamine, followed by hydrolysis of the reduction product to form 2-phosphino-2'-hydroxy-1,1'-binaphthyl (8). Further, this compound (8) is reacted with chlorophosphine (9) in the presence of triethylamine, whereby the phosphine compound (I) of the present invention is prepared.

Workup

  1. customfollowed by hydrolysis of the reduction product

Sources & evidence

ORD record
ord-36ae5dd7474647d4b70515b30f323079
Source dataset
uspto-grants-1996_06
Patent number
US05530150

Reaction notes

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