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

HRID 356531Notes

Reaction equation

HRID 356531 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](OC)(=[O:29])[CH2:25][C:26]([CH3:28])=[O:27].[H-].[Na+].C([Li])CCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]2([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[O:18][C:24](=[O:29])[CH:25]=[C:26]([OH:27])[CH2:28]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 219385753-(3-Benzyloxy-phenyl)-1-cyclopentyl-propan-1-oneHCID 178418339Butyllithium

Product 1

HCID 546822726-[2-(3-Benzyloxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 6 using 3-(3-benzyloxy-phenyl)-1-cyclopentyl-propan-1-one (3.3 g, 11.3 mmol) from Example YYYY, 2.45 mL (22.7 mmcl) of methyl acetoacetate, 0.93 g (23.2 mmol) of 60% NaH dispersion in mineral oil, 14.5 mL (1.6M, 23.2 mmol) of n-butyllithium and 40 mL of THF. The reaction mixture was quenched with 5 mL HOAc and the mixture was worked up in the normal manner.

Workup

  1. customThe reaction mixture was quenched with 5 mL HOAc

Sources & evidence

ORD record
ord-a5a4c125efaa42b2af1229bc90891ad9
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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