Nitromethane → HCID 10012389, compound

HRID 1741999Notes

Reaction equation

HRID 1741999 reaction equation
[CH:1]1[CH:6]=[C:5]2C=CC(O)=[C:10]([C:11]3C4C(=CC=CC=4)C=CC=3O)[C:4]2=[CH:3][CH:2]=1.CC(C)([O-])C.CC(C)([O-])C.CC(C)([O-:36])C.[La+3].[N+:39](C)([O-:41])=[O:40]>O1CCCC1>[CH:4]1([CH:10]([OH:36])[CH2:11][N+:39]([O-:41])=[O:40])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 11762BinolHCID 86748053HCID 86748053, compound

Product 1

HCID 10012389HCID 10012389, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 159 mg (0.56 mmol) of (S)-2,2'-dihydroxy-1,1'-binaphthyl were added to 7.56 cm3 of a THF solution of lanthanum tri-t-butoxide (4.9×10-2 mol.dm-3 as a monomer) at room temperature, followed by stirring for 2 hours. In the presence of 10 mol % (based on La) of the resultant solution, 2 mol equivalents (based on La) of LiCl and 10 mol equivalents (based on La) water, cyclohexylaldehyde reacted with nitromethane (10 equivalents) in tetrahydrofuran at -42° C. for 18 hours to give 1-cyclohexyl-2-nitroethanol represented by the formula ##STR8## With an optical purity of 90% ee. in a yield of 91%.

Sources & evidence

ORD record
ord-e84a7d077ca94223837d9ceb1314615b
Source dataset
uspto-grants-1994_08
Patent number
US05336653

Reaction notes

Loading…