Sodium hydride → HCID 9951935, compound

HRID 1018111Notes

Reaction equation

HRID 1018111 reaction equation
[H-].[Na+].C([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13]P(OCC)(OCC)=O)=[CH:9][CH:8]=1)C.[CH2:23]([O:25][CH2:26][C:27]1([CH3:40])[CH2:33][CH2:32][CH2:31][S:30][C:29]2[CH:34]=[C:35]([CH:38]=O)[CH:36]=[CH:37][C:28]1=2)[CH3:24]>CN(C=O)C>[CH2:23]([O:25][CH2:26][C:27]1([CH3:40])[CH2:33][CH2:32][CH2:31][S:30][C:29]2[CH:34]=[C:35](/[CH:38]=[CH:13]/[C:10]3[CH:9]=[CH:8][C:7]([C:6]([OH:5])=[O:22])=[CH:12][CH:11]=3)[CH:36]=[CH:37][C:28]1=2)[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10979490Ethyl 4-((diethoxyphosphoryl)methyl)benzoateHCID 18406107HCID 18406107, compound

Product 1

HCID 9951935HCID 9951935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

85 mg of NaH (ca. 1.4 eq., 50% in mineral oil) was added to a solution of 534 mg (1.4 eq.) of 4-(diethoxyphosphorylmethyl)-benzoic acid ethyl ester in 1.9 ml of abs. DMF at 0° C. The mixture was stirred at 0° C. for 0.5 h and at room temperature for 1.5 h. After cooling to 0° C., 336 mg (1.27 mmol) of 5-ethoxymethyl-5-methyl-2,3,4,5-tetrahydrobenzo[b]thiepine-8-carbaldehyde, dissolved in 1 ml of DMF, was added and allowed to react for 2 h at room temperature. The mixture was then poured onto crushed ice, extracted twice with diethylether, the organic phase was washed with water, dried over magnesium sulfate, filtrated and evaporated to dryness. Purification of the residue by flash chromatography (silica gel, hexane/ethylacetate 95/5) afforded 409 mg of pure, colorless title compound.

Workup

  1. customat 0° C
  2. temperatureAfter cooling to 0° C.
  3. additionwas added
  4. customto react for 2 h at room temperature
  5. additionThe mixture was then poured
  6. customonto crushed ice
  7. extractionextracted twice with diethylether
  8. washthe organic phase was washed with water
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltrated
  11. customevaporated to dryness
  12. customPurification of the residue by flash chromatography (silica gel, hexane/ethylacetate 95/5)

Sources & evidence

ORD record
ord-083b52088d924b3e80ea5aa93de34965
Source dataset
uspto-grants-2002_11
Patent number
US06479670B1

Reaction notes

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