Methyl acetoacetate → 4-Hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

HRID 1003841Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:36])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[C:22](OC)[CH:21]=2)=[CH:11][C:10]=1[O:37][CH3:38])C1C=CC=CC=1.[H-].[Na+].[C:41](OC)(=[O:46])[CH2:42][C:43]([CH3:45])=[O:44].C([Li])CCC.C1C[O:57][CH2:56]C1>>[OH:44][C:43]1[CH2:45][C:17]([CH2:16][CH2:15][C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:37][CH3:38])[CH:11]=2)([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:57][CH3:56])[CH:21]=2)[O:36][C:41](=[O:46])[CH:42]=1

Participants

Reactant 5

HCID 7757Methyl acetoacetate

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 187986361,5-Bis-(4-benzyloxy-3-methoxy-phenyl)-pentan-3-one

HCID 178418339Butyllithium

Product 1

HCID 546822754-Hydroxy-6,6-bis-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared as described in General Method 6 using 3.72 g (7.3 mmol) of 1,5-bis-(4-benzyloxy-3-methoxy-phenyl)-pentan-3-one (prepared in Example I), 0.32 g (8.0 mmol) of 60% NaH dispersion in mineral oil, 0.85 g (7.3 mmol) of methyl acetoacetate, 5.0 mL (1.6 M, 8.0 mmol) of n-butyllithium and 100 mL of THF. The reaction mixture was stirred for 12 hours at room temperature and worked up in the usual manner.

Sources & evidence

ORD record: ord-5ee6aff19f9f4a2e9334786cd8b57042
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046355

Reaction notes

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