Hydrochloric Acid → HCID 11601217, compound

HRID 2265772Notes

Reaction equation

HRID 2265772 reaction equation
C([O:3][C:4](=O)[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[C:6](OCC)=[O:7])C.CC(C[AlH]CC(C)C)C.Cl.C(OCC)(=O)C>C1COCC1>[Br:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH:5]([CH2:4][OH:3])[CH2:6][OH:7])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 10860456Diethyl 2-(4-bromobenzyl)malonate

Product 1

HCID 11601217HCID 11601217, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromo-benzyl)-malonic acid diethyl ester 21 (1.5 g, 3.8 mmol) was dissolved in 5 mL THF and the solution was added slowly to DIBALH (1M in toluene, 25 mL) via a syringe at 0° C. and stirred at the same temperature for 3 hr. HCl (2N, 50 mL) was then added to break the complex. After standard work up with ethyl acetate, crude product 22 (0.9 g, 99%) was obtained, which was used directly for the next step without further purification: 1H NMR δ 7.39 (d, 2H, J=8.2 Hz), 7.04 (d, 2H, J=8.2 Hz), 3.60 (m, 4H), 2.55 (d, 2H, J=7.4 Hz), 1.96 (m, 1H).

Sources & evidence

ORD record
ord-aacfc1bd004d489aa1ad7c35d3870167
Source dataset
uspto-grants-2010_12
Patent number
US07858072B2

Reaction notes

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