Sodium hydride → HCID 90403911, compound

HRID 1049286Notes

Reaction equation

HRID 1049286 reaction equation
[H-].[Na+].[C:3]([O:12][CH:13]([CH3:15])[CH3:14])(=[O:11])[CH2:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6].[C:16]1([CH2:32]C2C=C(C)C=CC=2S([O-])(=O)=O)([CH2:20]C2C=C(C)C=CC=2S([O-])(=O)=O)[CH2:19][CH2:18][CH2:17]1>CN(C=O)C>[CH2:20]1[C:16]2([CH2:19][CH2:18][CH2:17]2)[CH2:32][C:4]1([C:5]([O:7][CH:8]([CH3:9])[CH3:10])=[O:6])[C:3]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83223Diisopropyl malonateHCID 131736003HCID 131736003, compound

Product 1

HCID 90403911HCID 90403911, compoundYield 138.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of NaH (60% in mineral oil, 1.394 g, 34.9 mmol) in DMF (35 mL) was treated drop-wise with diisopropyl malonate (5.30 mL, 27.9 mmol) followed by cyclobutane-1,1-diylbis(methylene)bis(4-methylbenzenesulfonate) (5.92 g, 13.94 mmol) and KI (0.231 g, 1.394 mmol) and heated at 140° C. overnight. The mixture was cooled to RT, poured on satd. NH4Cl, extracted with hexane (2×) and the combined organics were washed with H2O, dried over MgSO4 and concentrated to dryness to afford crude diisopropyl spiro[3.3]heptane-2,2-dicarboxylate (5.17 g, 138%) which was carried on without purification.

Workup

  1. temperatureThe mixture was cooled to RT
  2. additionpoured on satd
  3. extractionNH4Cl, extracted with hexane (2×)
  4. washthe combined organics were washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-38df9cfc3d5546c29e76d13efd11a24d
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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