Ethylamine → 3-Benzyloxy-2-methyl-4-pyrone

HRID 465015Notes

Reaction equation

HRID 465015 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][O:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C(=O)C=CN(C)C=1C.C(N)C.C(N)CC.C(N)(C)C.C(N)CCC.Cl.C(N)CCCCC.Cl.CN>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][O:11][C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 7

HCID 6341EthylamineHCID 6363IsopropylamineHCID 7852PropylamineHCID 8007ButylamineHCID 673421-Hexanamine, hydrochlorideHCID 6364545Methylamine hydrochlorideHCID 86740388HCID 86740388, compound3×

Product 1

HCID 14901193-Benzyloxy-2-methyl-4-pyrone

Procedure

3-Benzyloxy-2-methyl-4-pyrone is prepared as described in (C) and is reacted with ethylamine, n-propylamine, isopropylamine, n-butylamine and n-hexylamine hydrochloride under similar conditions to those described in (C) for methylamine hydrochloride. The reaction mixture is worked up and the hydroxy group deprotected as described in (C) to give the following compounds:

Workup

  1. customto give the following compounds

Sources & evidence

ORD record
ord-53f392f094c14b1391495cd98aa7d375
Source dataset
uspto-grants-1985_10
Patent number
US04550101

Reaction notes

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