Resorcinol → 3-Hydroxy-8,9,10,11-tetrahydrobenzo[b]cyclohepta[d]pyran-6(7H)-one

HRID 2361528ノート

反応式

HRID 2361528 の反応式
[C:1]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=O)([O:3][CH2:4][CH3:5])=[O:2].[C:14]1([CH:21]=CC=[C:17](O)[CH:16]=1)[OH:15]>CS(O)(=O)=O>[OH:15][C:14]1[CH:21]=[C:4]2[C:5]([C:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:6]=3[C:1](=[O:2])[O:3]2)=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 5054ResorcinolHCID 279795Ethyl 2-oxocycloheptane-1-carboxylate

生成物 1

HCID 54158673-Hydroxy-8,9,10,11-tetrahydrobenzo[b]cyclohepta[d]pyran-6(7H)-one収率 78%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

実験手順

The first stage consists of condensing 2-carbetoxycycloheptanone with resorcinol in methanesulphonic acid, the reaction is taken to 25° C. for 4 hours. The intermediate 3-hydroxy-8,9,10,11-tetrahydrocyclohepta[c]chromen-6(7H)-one thus formed precipitates by adding ethanol then water then it is isolated by filtration, dried under vacuum at 60° C. and a yield of 78% is obtained. In a second stage, sulphonylisocyanate chloride is converted, in toluenic solution, to sulphamoyl chloride by the action of the formic acid, then condensed with the previous intermediate dissolved in N,N-dimethylacetamide (DMA). The reaction medium is treated with water and extracted with 2-methyltetrahydrofurane (2-MeTHF). The crude compound 1 is then obtained by filtration of the precipitate obtained by adding methylcyclohexane to the organic phase. Finally, pure compound 1 is obtained by recrystallization of the crude product by dissolution in acetone while hot and precipitation by adding methylcyclohexane (the addition of the antisolvent methylcyclohexane having the main purpose of increasing the yield).

出典と根拠

ORDレコード
ord-588f76239d21446fa0c57ab63196fbc3
出典データセット
uspto-grants-2014_04
特許番号
US08691281B2

反応ノート

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