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

HRID 356486노트

반응식

HRID 356486 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customquenched with aqueous NH4Cl

출처 및 근거

ORD 기록
ord-40a37df1d5424bec9c230b2caf42fe52
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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