Acetic Acid → HCID 67486385, compound

HRID 1755176Notes

Reaction equation

HRID 1755176 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[C:17](=[O:18])[O:16][C:15]([CH3:20])([CH3:19])[O:14][C:13]2=[O:21])=O)=[CH:6][CH:5]=1.CC(O)=O.[BH4-].[Na+]>C(Cl)Cl.CCOCC>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:12]2[C:13](=[O:21])[O:14][C:15]([CH3:19])([CH3:20])[O:16][C:17]2=[O:18])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 67486722HCID 67486722, compound

Product 1

HCID 67486385HCID 67486385, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of crude 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-benzoic acid methyl ester from step A was dissolved in DCM (50 mL) and AcOH (5 mL) and chilled to ice-bath temperature. To the solution was added portion-wise, over 30 min, NaBH4 (722 mg, 19.1 mmol). The reaction mixture was allowed to warm to RT overnight. The mixture was quenched with water, stirred for 10 min then extracted with DCM. The organic solution was dried over Na2SO4 and concentrated to afford an off-white solid that was suspended in Et2O to give pure 4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-benzoic acid methyl ester as a white solid (2.24 g, 60%). 1H NMR (500 MHz, DMSO-d6): δ 7.87 (d, J=8 Hz, 2H), 7.43 (d, J=8 Hz, 2H), 4.86 (t, 7.87 (d, J=5 Hz, 1H), 2H), 3.84 (s, 3H), 3.35 (d, J=5 Hz, 2H), 1.83 (s, 3H), 1.64 (s, 3H)

Workup

  1. additionTo the solution was added portion-wise
  2. customThe mixture was quenched with water
  3. extractionthen extracted with DCM
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated
  6. customto afford an off-white solid

Sources & evidence

ORD record
ord-149159aa2e4047259a1f1bae920481f4
Source dataset
uspto-grants-2015_10
Patent number
US09169201B2

Reaction notes

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