Tetrahydrofuran → morpholine 5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide

HRID 1463925Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].C(O[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:24]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C#C.[O:38]1CC[CH2:40][CH2:39]1>O>[NH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:31]([O:30][C:24]1[CH:23]=[CH:28][CH:27]=[CH:26][C:25]=1[C:29]#[C:40][C:39](=[O:38])[CH2:2][C:1]([NH2:4])=[O:3])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Acetyl morpholine (546 ul, 4.72 mmole) was dissolved in 10 ml dry tetrahydrofuran in an oven dried 50 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C. and was treated slowly dropwise with lithium diisopropylamide (3.2 ml, 4.72 mmole). The mixture was stirred 30 minutes at 0° C. and was treated with methyl-2-benzyloxyphenyl propiolate (600 mg, 2.25 mmole) in 2 ml dry tetrahydrofuran. The reaction mixture was stirred for 1 hour at 0° C. and was diluted with 10 ml water. The volatiles were removed in vacuo and the residue was crystallized from diethyl ether/methanol (20:1). The tan solid was collected, was washed with diethyl ether, and was dried to afford 500 mg (61%) of morpholine-5-(2-Benzyloxyphenyl)-3-oxo-pent-4-ynamide as a tan solid. Melting Point: 224°-227° C.

Workup

dry with materialdried 50 ml two neck round bottom flask under nitrogen
stirringThe reaction mixture was stirred for 1 hour at 0° C.
customThe volatiles were removed in vacuo
customthe residue was crystallized from diethyl ether/methanol (20:1)
customThe tan solid was collected
washwas washed with diethyl ether
customwas dried

Sources & evidence

ORD record: ord-c351075d065040a1ba1d312e4d965ae0
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05302613

Reaction notes

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