Phthalimide → 2-Phthalimidomethyl-8-methoxy-chroman

HRID 1077708Notes

Reaction equation

HRID 1077708 reaction equation
O[CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[O:4]1.[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:15]1(=[O:25])[N:19]([CH2:2][CH:3]2[CH2:12][CH2:11][C:10]3[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=3)[O:4]2)[C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 234318182-Hydroxymethyl-8-methoxy-chroman

Product 1

HCID 214673652-Phthalimidomethyl-8-methoxy-chromanYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By reacting the compound from Example II with phthalimide in the presence of equimolar amounts of triphenylphosphane and diethyl azodicarboxylate in tetrahydrofuran, the desired product is obtained in 80% yield in the form of a syrup, which is further reacted directly. Rf =0.46 (toluene/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-7ea37a15456847099a4d1a2fd45cf8ab
Source dataset
uspto-grants-1996_08
Patent number
US05545643

Reaction notes

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