Ethyl Acetoacetate → 6-[1,1'-Biphenyl]-4-yl-6-butyl-5,6-dihydro-4-hydroxy-2H-pyran-2-one

HRID 1585389Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].[C:17]1([C:29]2[CH:34]=[CH:33]C=[CH:31][CH:30]=2)[CH:22]=[CH:21][C:20](C(=O)CCCC)=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[C:29]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:34]=[CH:33][C:9]([C:8]2([CH2:12][CH2:13][CH2:14][CH3:15])[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: -78 °C

Procedure

The title compound was prepared as described in General Method 1 using 13 g ethyl acetoacetate, 5.3 g of NaH 60% dispersion in oil, 60 mL of 1.6M n-butyl lithium in hexane, 21 g of 1-[1,1'-biphenyl]-4-yl-1-pentanone and 300 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred 15 minutes at -78° C. and 2 hours at room temperature. The crude reaction mixture afforded a solid which was washed with CH2Cl2 and two times with ethyl acetate (m.p. 165-170° C.). 1H NMR (d6 -DMSO) δ 0.7-1. 9 (m, 7 H), 2.0 (m, 2 H), 3.0 (s, 2 H), 4.9 (s, 1 H), 7.3-7.8 (m, 9 H), 11.3 (s, 1 H).

Workup

customThe crude reaction mixture
customafforded a solid which
washwas washed with CH2Cl2 and two times with ethyl acetate (m.p. 165-170° C.)

Sources & evidence

ORD record: ord-0e1cbe4537244f16bd8474649d34bc73
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05936128

Reaction notes

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