Tetrahydrofuran → HCID 62390561, compound

HRID 1876890Notes

Reaction equation

HRID 1876890 reaction equation
CC(C)([O-])C.[K+].O1CCCC1.[C:12]([CH2:14]P(=O)(OCC)OCC)#[N:13].[O:23]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25][CH2:24]1>>[O:23]1[CH2:28][CH2:27][CH:26](/[CH:29]=[CH:14]/[C:12]#[N:13])[CH2:25][CH2:24]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 75676Diethyl (cyanomethyl)phosphonateHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 62390561HCID 62390561, compound

Procedure

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (9.20 mL, 0.00920 mol) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (1.56 mL, 0.00965 mol) in tetrahydrofuran (11.73 mL, 0.1447 mol). The reaction was warmed to room temperature and then cooled at 0° C. again. To the reaction mixture was added a solution of tetrahydro-2H-pyran-4-carbaldehyde (1.0 g, 0.0088 mol) in tetrahydrofuran (2.35 mL, 0.0289 mol). The reaction was allowed to warm up to room temperature and stirred overnight. After being quenched with water, the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and evaporated to dryness. The crude mixture was used directly in next step. LCMS (M+H) 138.0.

Workup

  1. temperaturecooled at 0° C. again
  2. temperatureto warm up to room temperature
  3. customAfter being quenched with water
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-91e4be472def4fdfb71014f3cca1c91f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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