Methyl acetoacetate → HCID 10029608, compound

HRID 359563Notes

Reaction equation

HRID 359563 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][C:10]([CH3:23])([CH3:22])[C:9]=2/[CH:24]=[CH:25]/[CH:26]=[O:27])=[CH:4][C:3]=1[CH3:28].[Li+].CC([N-]C(C)C)C.[C:37]([O:43][CH3:44])(=[O:42])[CH2:38][C:39]([CH3:41])=[O:40]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])[CH2:11][C:10]([CH3:22])([CH3:23])[C:9]=2/[CH:24]=[CH:25]/[CH:26]([OH:27])[CH2:41][C:39](=[O:40])[CH2:38][C:37]([O:43][CH3:44])=[O:42])=[CH:4][C:3]=1[CH3:28]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 10069715HCID 10069715, compound

Product 1

HCID 10029608HCID 10029608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similiar to Scheme I, 19 (13.45 g, 33.4 mmol) was treated with LDA-derived dianion of methyl acetoacetate (40.1 mmol) in THF and, after workup and purification by HPLC. using 4:1 hexanes:EtOAc as eluent provided 7.8 g of an orange color oil.

Workup

  1. customafter workup and purification by HPLC
  2. customEtOAc as eluent provided 7.8 g of an orange color oil

Sources & evidence

ORD record
ord-bc3167d5b03749e6a9fbf0715e4dbe61
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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