Methyl acetoacetate → HCID 54682293, compound

HRID 1003846Notes

Reaction equation

HRID 1003846 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.C([Si](C)(C)[O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])[CH:25]=[CH:26][CH:27]=1)(C)(C)C.[OH-].[Na+]>C1COCC1>[OH:4][C:3]1[CH2:5][C:30]([CH2:29][CH2:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([OH:21])[CH:23]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:31][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 5

HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 18798645HCID 18798645, compoundHCID 178418339Butyllithium

Product 1

HCID 54682293HCID 54682293, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound was prepared as described in General Methods 6 and 7 using 2.4 mL (22.2 mmol) of methyl acetoacetate, 1.02 g (25.5 mmol) of 60% sodium hydride, 16 mL (25.6 mmol) of 1.6 M n-butyllithium, 6.2 g (18.2 mmol) of 3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-phenyl-propan-1-one from Example Q and 180 mL of THF. After standard work-up, the crude aldol product was dissolved in THF (60 mL), treated with 0.2N NaOH (500 mL), and stirred at room temperature. The title compound was isolated via the normal procedure. 1H NMR (CDCl3) δ 2.21 (m, 2 H), 2.38 (m, 1 H), 2.61 (m, 1 H), 2.93 (dd, 2 H), 3.28 (dd, 2 H), 6.54-6.65 (m, 3 H), 7.06 (m, 1 H), 7.28-7.40 (m, 6 H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-535961cba6014ba5b4334282e068d0ba
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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