Ethyl Acetate → HCID 19848771, compound

HRID 1608422Notes

Reaction equation

HRID 1608422 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8]C1C=C(CNCCCNCCCCNCCCN)C=CC=1O.O[C:32]1([CH3:58])[CH2:37][CH:36]([CH:38]([CH3:42])[CH2:39][C:40]#[N:41])[C:35]2[CH:43]=[CH:44][C:45]([CH:47]([CH2:49][CH2:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH3:48])=[CH:46][C:34]=2[O:33]1.C(OCC)(=O)C>O1CCCC1>[NH2:41][CH2:40][CH2:39][CH:38]([CH:36]1[C:35]2[C:43]([OH:8])=[CH:44][C:45]([CH:47]([CH2:49][CH2:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH3:48])=[CH:46][C:34]=2[O:33][CH:32]([CH3:58])[CH2:37]1)[CH3:42]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 131714007HCID 131714007, compound

Product 1

HCID 19848771HCID 19848771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under anhydrous conditions and in a nitrogen atmosphere, to a solution of 190 mg (5 mmole) lithium aluminum hydride in 50 ml tetrahydrofuran at 10° C. is added dropwise a solution of 1.885 g (5 mmole) dl-5-hydroxy-4-(1-methyl-2-cyanoethyl)-2-methyl-7-(5-phenyl-2-pentyl)-3,4-dihydro-2H-benzopyran in 25 ml of tetrahydrofuran. After the addition is complete, the mixture is stirred at room temperature for 6 hours. Ethyl acetate is added to consume the unreacted hydride. The reaction mixture is evaporated to dryness, the residue partitioned between water and methylene chloride and the organic layer dried over anhydrous magnesium sulfate. The solvent is evaporated to provide the title compound as the free base.

Workup

  1. additionAfter the addition
  2. customto consume the unreacted hydride
  3. customThe reaction mixture is evaporated to dryness
  4. customthe residue partitioned between water and methylene chloride
  5. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-ddd217b8960c4722851c4dc7dde8e414
Source dataset
uspto-grants-1989_09
Patent number
US04870084

Reaction notes

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