Tetrabutylammonium Fluoride → HCID 22345111, compound
Reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]1[C:22]3[C:17](=[CH:18][C:19]([CH:23]=[CH2:24])=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=1[O:25][Si](C(C)(C)C)(C)C)=[C:8]([O:33][Si](C(C)(C)C)(C)C)[CH:7]=[CH:6]2)=[CH2:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH:23]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[C:13]([C:9]1[C:10]3[C:5](=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:12][CH:11]=3)[CH:6]=[CH:7][C:8]=1[OH:33])=[C:14]([OH:25])[CH:15]=[CH:16]2)=[CH2:24]Participants
Procedure
An optically active binaphthol (VII) is reacted with bromine in acetic anhydride to obtain 6,6'-dibromo-2,2'-dihydroxy-1,1'-binaphthyl (XII). The hydroxyl groups of compound (XII) are protected using tert-butyldimethylsilyl oxytriflate (TBDMSOTf) and 2,6-lutidine to obtain 6,6'-dibromo-2,2'-bis(tert-butyldimethylsilyloxy)-1,1'-binaphthyl (XIII). Compound (XIII) is converted to an anion form using sec-butyllithium (sec-BuLi), and dimethylformamide (DMF) is caused to act thereon to obtain 6,6'-diformyl-2,2'-bis(tert-butyldimethylsilyloxy)-1,1'-binaphthyl (XIV). Compound (XIV) is reacted with triphenylmethylphosphonium bromide (Ph3P+CH3Br-) and potassium t-butoxide (t-BuOK) to obtain 6,6'-divinyl-2,2'-bis(tert-butyldimethylsilyloxy)-1,1'-binaphthyl (XV). Compound (XV) is reacted with tetrabutylammonium fluoride (TBAF) for silyl removal to obtain 6,6'-divinyl-2,2'-dihydroxy-1,1'-binaphthyl, which is heated together with phosphorus trichloride to obtain 6,6'-divinyl-1,1'-binaphthalene-2,2'-dioxychlorophosphine (XVI). The 6,6'-divinyl-1,1'-binaphthalene-2,2'-dioxychlorophosphine (XVI) is reacted with 2'-diphenylphosphino-2-hydroxy-1,1'-binaphthyl (XI) in the presence of triethylamine (NEt3) to obtain 2'-diphenylphosphino-1,1'-binaphthalen-2-yloxy(6,6'-divinyl-1,1'-binaphthalene-2,2'-diyloxy)phosphine (XVII).
Sources & evidence
- ORD record
- ord-a0defb574d254641b655bc63dace402a
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06143834
Reaction notes
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