Triphenylphosphine → HCID 68965484, compound

HRID 2116181Notes

Reaction equation

HRID 2116181 reaction equation
CC1C=CC(S(OCC2CC3C=CC=C(/C=C/C4C=CC=CC=4)C=3O2)(=O)=O)=CC=1.[N-]=[N+]=[N-].[Na+].[C:34]1(/[CH:40]=[CH:41]/[C:42]2[C:50]3[O:49][CH:48]([CH2:51][N:52]=[N+]=[N-])[CH2:47][C:46]=3[CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:34]1(/[CH:40]=[CH:41]/[C:42]2[C:50]3[O:49][CH:48]([CH2:51][NH2:52])[CH2:47][C:46]=3[CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 86599129HCID 86599129, compoundHCID 86599237HCID 86599237, compound2×

Product 1

HCID 68965484HCID 68965484, compoundYield 34%

Procedure

Treatment of (±)-{7-[(E)-2-phenylvinyl]-2,3-dihydro-1-benzofuran-2-yl}methyl 4-methylbenzenesulfonate (6.53 g, 16.06 mmol) with sodium azide (4.17 g, 64.25 mmol) generally according to the procedure described for Intermediate 98 afforded (±)-(7-[(E)-2-phenylvinyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide. Treatment of (±)-{7-[(E)-2-phenylvinyl]-2,3-dihydro-1-benzofuran-2-yl}methyl azide (2.2 g, 7.9 mmol) with triphenylphosphine (2.08 g, 7.9 mmol) generally according to the procedure described for Example 21 afforded 0.675 g (34%) of (±)-1-{7-[(E)-2-phenylvinyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine as a white solid, hydrochloride salt. mp 209-211° C.; Anal. calcd. for C17H17NOHCl: C, 70.95; H, 6.3; N, 4.87. Found: C, 69.63; H, 6.46; N, 4.72.

Sources & evidence

ORD record
ord-b030a0d647d448b3a837e430af1a6644
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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