Sodium Hydroxide → HCID 59511941, compound

HRID 1157667Notes

Reaction equation

HRID 1157667 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH2:11][C:12]([CH3:18])([CH3:17])[CH2:13]C(O)=O)=[CH:9][C:4]=2[O:3][CH2:2]1.C([N:23](CC)C(C)C)(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:11][C:12]([CH3:18])([CH3:17])[CH2:13][N:23]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59511945HCID 59511945, compound

Product 1

HCID 59511941HCID 59511941, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-(1,3-benzodioxol-5-yl)-3,3-dimethyl-5-oxopentanoic acid (444 mg, 1.68 mmol) and N,N-diisopropylethylamine (0.292 mL, 1.68 mmol) in chloroform, add diphenylphosphorylazide (0.364 mL, 1.68 mmol). Stir at room temperature for 2 days, then treat with 2N NaOH. After 1 h, dilute the reaction with chloroform and water, then separate the organic layer and dry with magnesium sulfate, filter, and concentrate under reduced pressure to obtain 132 mg (36%) of the title compound. MS: 218 [M+H]+; 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 1H), 7.20-7.24 (m, 1H), 6.78-6.81 (m, 1H), 6.00 (s, 2H), 3.75-3.74 (m, 2H), 2.72-2.71 (m, 2H) and 1.16 (s, 6H).

Workup

  1. waitAfter 1 h
  2. additiondilute
  3. customseparate the organic layer
  4. dry with materialdry with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-996bc389a3ba42a8bdefda9830dbcc36
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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