Methyl acetoacetate → HCID 54682266, compound

HRID 356489Notes

Reaction equation

HRID 356489 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:16]([Si:20]([CH3:42])([CH3:41])[O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:40])[CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:27][CH:26]=1)([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([Si:20]([CH3:42])([CH3:41])[O:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[O:40][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:29][CH:30]=1)([CH3:18])([CH3:17])[CH3:19]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187986931-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-3-phenyl-propan-1-oneHCID 178418339Butyllithium

Product 1

HCID 54682266HCID 54682266, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Methods 6 and 7 using 2.5 mL (23.2 mmol) of methyl acetoacetate, 0.96 g (24 mmol) of 60% sodium hydride, 15 mL (24 mmol) of 1.6M n-butyllithium, 4.5 g (11.7 mmol) of 1-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxyl -phenyl}-3-phenyl-propan-1-one from Example O and 100 mL of THF. Purification by silica gel chromatography, eluting with EtOAc:hexane (25:75 to 50:50) gave the title compound. 1H NMR (CDCl3) δ 0.0 (s, 6 H), 0.81 (s, 9 H), 2.17 (m, 2 H), 2.42 (m, 1 H), 2.63 (m, 1 H), 2.85 (dd, 2 H), 3.22 (dd, 2 H), 3.86-3.96 (m, 4 H), 6.80-7.19 (m, 9 H).

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography
  3. washeluting with EtOAc:hexane (25:75 to 50:50)

Sources & evidence

ORD record
ord-dddeb94482fb4719b0418e11587215bf
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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