Sodium Hydroxide → HCID 57983418, compound

HRID 1868919Notes

Reaction equation

HRID 1868919 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:25])([CH3:24])[C:9](=[O:23])[C:10]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[C:11]2[OH:14])=[CH:6][CH:5]=1>C1COCC1.C(Cl)Cl>[Br:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([CH3:25])([CH3:24])[C:9](=[O:23])[C:10]([C:15](=[O:22])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:11]2[OH:14])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57983485HCID 57983485, compound

Product 1

HCID 57983418HCID 57983418, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous NaOH (5M, 2.0 mL) was added to a solution of methyl 4-(7-bromo-1-hydroxy-4,4-dimethyl-3-oxo-3,4-dihydronaphthalen-2-yl)-4-oxobutanoate (0.061 g, 0.16 mmol) in THF (1.5 mL). The mixture was stirred for 15 minutes at room temperature, diluted with DCM, and extracted with water. The water phase was acidified to pH=1 using aqueous HCl (5M) and extracted with EtOAc. The combined organic layers were dried over MgSO4 and evaporated. The product was rinsed with diethyl ether and dried to afford the title compound in 31% yield. 1H-NMR (300 MHz, DMSO-d6) δ ppm 12.19 (1H, br. s.), 8.17, 8.16 (1H, 2 s), 7.91-7.88 (1H, m), 7.75-7.72 (1H, m), 3.45-3.35 (2H, m, partially covered by HDO signal), 2.60-2.56 (2H, m), 1.54 (6H, br. s.). MS m/z: 368 (M+).

Workup

  1. extractionextracted with water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated
  5. washThe product was rinsed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-a73d8fed5283417593ba35b8b65a8e0b
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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