HCID 20779598, compound → HCID 86597850, compound

HRID 2180584Notes

Reaction equation

HRID 2180584 reaction equation
[C:1]([C:5]1[C:14]2[CH:13]=[C:12](/[C:15](/[CH2:20][CH3:21])=[C:16](/[F:19])\[CH:17]=O)[C:11]([O:22][CH2:23][CH3:24])=[CH:10][C:9]=2[C:8]([CH3:26])([CH3:25])[CH2:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(P([CH2:33]/[C:34](/[CH3:41])=[CH:35]\[C:36]([O:38][CH2:39][CH3:40])=[O:37])(CC)=O)C>C1COCC1.CN1C(=O)N(C)CCC1>[C:1]([C:5]1[C:14]2[CH:13]=[C:12](/[C:15](/[CH2:20][CH3:21])=[C:16](/[F:19])\[CH:17]=[CH:33]\[C:34](\[CH3:41])=[CH:35]\[C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:11]([O:22][CH2:23][CH3:24])=[CH:10][C:9]=2[C:8]([CH3:25])([CH3:26])[CH2:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 20779598HCID 20779598, compoundHCID 86597846HCID 86597846, compound

Product 1

HCID 86597850HCID 86597850, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

As described in General Procedure I-1, (E)-3-(8-tert-butyl-3-ethoxy-5,5-dimethyl-5,6-dihydronaphthalen-2-yl)-2-fluoro-pent-2-enal (Compound A-65, 435 mg, 1.21 mmol) reacted with the ylide of ethyl 4-(diethylphosphoryl)-3-methylbut-2Z-enoate (1.07 g, 4.05 mmol) in THF (10 mL) and DMPU (5 mL) to produce the title compound as an oil after purification by flash chromatography (silica gel, 1% to 2% ethyl acetate in hexane).

Sources & evidence

ORD record
ord-ed99f14b40484853b5d3b94abd8e79f3
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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