Methyl acetoacetate → 4-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 356486ノート

反応式

HRID 356486 の反応式
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:34])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H-].[Na+].[C:37](OC)(=[O:42])[CH2:38][C:39]([CH3:41])=[O:40].C([Li])CCC>C1COCC1>[OH:40][C:39]1[CH2:41][C:17]([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[O:34][C:37](=[O:42])[CH:38]=1

参加物

6

反応物 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 541582871,5-Bis (4-benzyloxy-phenyl)-pentan-3-oneHCID 178418339Butyllithium

生成物 1

HCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The title compound was prepared as described in General Method 6 using 11.2 g (25 mmol) of 1,5-bis (4-benzyloxy-phenyl)-pentan-3-one (prepared in Example H), 1.0 g (25 mmol) of 60% NaH dispersion in mineral oil, 2.88 g (25 mmol) of methyl acetoacetate, 15.6 mL (1.6M, 25 mmol) of n-butyllithium and 300 mL of THF. The reaction mixture was stirred for 12 hours at room temperature, quenched with aqueous NH4Cl, and worked up in the usual manner.

後処理

  1. customquenched with aqueous NH4Cl

出典と根拠

ORDレコード
ord-40a37df1d5424bec9c230b2caf42fe52
出典データセット
uspto-grants-1998_11
特許番号
US05834506

反応ノート

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