Acetone Cyanohydrin → HCID 68964162, compound

HRID 2116410Notes

Reaction equation

HRID 2116410 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18]O)[CH2:14][C:13]=2[CH:12]=[C:11]([F:20])[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:40]([C:47](OCC)=O)=NC(OCC)=O.OC(C)(C)C#N>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18][CH2:47][NH2:40])[CH2:14][C:13]=2[CH:12]=[C:11]([F:20])[CH:10]=1

Participants

5

Reactant 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 68961693HCID 68961693, compound

Product 1

HCID 68964162HCID 68964162, compoundYield 17.1%

Procedure

Treatment of (±)-[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methanol (0.5 g, 1.9 mmol) with triphenylphosphine (1.23 g, 4.67 mmol), diethyl azodicarboxylate (0.82 g, 4.68 mmol), and 2-hydroxy-2-methylpropanenitrile (0.40 g, 4.68 mmol) generally according to the procedure described for Example 552 afforded 0.106 g (15%) of (±)-{2-[7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]ethyl}amine as a white solid, hydrochloride salt. mp 212-213° C.

Sources & evidence

ORD record
ord-ac6c4fb69a6942cfa2b00fa79900b672
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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