Pivalaldehyde → HCID 58859128, compound

HRID 1349468Notes

Reaction equation

HRID 1349468 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].[CH3:27][C:28]([CH3:32])([CH3:31])[CH:29]=[O:30].C([N-]C(C)C)(C)C.[Li+].O1CCCC1.C1CCCCC1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]([C:9]1[O:10][CH:11]=[C:12]([CH:29]([OH:30])[C:28]([CH3:32])([CH3:31])[CH3:27])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:8]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 58859119HCID 58859119, compoundHCID 86596933HCID 86596933, compound

Product 1

HCID 58859128HCID 58859128, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid 3-chlorobenzylamide (300 mg) obtained in Example 10, Step 1 and 2,2-dimethylpropionaldehyde (9 ml) in tetrahydrofuran (9 ml) was added dropwise 1.5 M lithium diisopropylamide-tetrahydrofuran/cyclohexane solution (4.5 ml) under nitrogen at −78° C. After stirring at the same temperature for 2 hr, the cooling bath was removed and 1N aqueous hydrochloric acid (15 ml) and ethyl acetate (25 ml) were added, and the mixture was warmed to room temperature. The organic layer was separated from the aqueous layer and extracted with ethyl acetate (25 ml). The combined organic layer was dried, concentrated and purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give 3-benzyloxy-5-(1-hydroxy-2,2-dimethylpropyl)-4-oxo-4H-pyran-2-carboxylic acid 3-chlorobenzylamide (0.22 g).

Workup

  1. customthe cooling bath was removed
  2. addition1N aqueous hydrochloric acid (15 ml) and ethyl acetate (25 ml) were added
  3. customThe organic layer was separated from the aqueous layer
  4. extractionextracted with ethyl acetate (25 ml)
  5. customThe combined organic layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-a3096683cf5d4c2a89fad35fee1c5d50
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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