Ammonium Chloride → HCID 10065478, compound

HRID 2219064Notes

Reaction equation

HRID 2219064 reaction equation
C(OP([CH:9]([F:11])[F:10])(=O)OCC)C.C([Li])(C)(C)C.[OH:17][C:18]1[CH:35]=[CH:34][C:33]2[C@:32]3([CH:36]=O)[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[CH2:27][C@H:26]([OH:38])[CH2:25]4)[CH2:22][CH2:21][C:20]=2[CH:19]=1.[Cl-].[NH4+]>C(COC)OC.CCCCC>[F:11][C:9]([F:10])=[CH:36][C@:32]12[CH2:31][CH2:30][C@@:28]3([CH3:29])[C@@H:24]([CH2:25][C@@H:26]([OH:38])[CH2:27]3)[C@@H:23]1[CH2:22][CH2:21][C:20]1[CH:19]=[C:18]([OH:17])[CH:35]=[CH:34][C:33]2=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2758305Phosphonic acid, (difluoromethyl)-, diethyl esterHCID 12095978HCID 12095978, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 10065478HCID 10065478, compound

Reagents, catalysts & solvents 2

HCID 8003PentaneSolvent2×HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-75 °C

Procedure

1.5 ml of dimethoxyethane (molecular sieve), 0.3 ml of pentane and 0.13 ml (0.77 mmol) of diethyl(difluoromethyl)-phosphonate are introduced into a reaction flask that was rendered inert, and cooled to about −75° C. After 0.72 ml (1.07 mmol) of tert-butyllithium (1.5 M in pentane) is added and after 30 minutes of reaction time, 0.14 g (0.31 mmol) of 3,16α-dihydroxy-estra-1,3,5(10)-triene-9-carbaldehyde, dissolved in a mixture of 1.5 ml of dimethoxyethane/0.3 ml of pentane, is added to the reaction solution. The reaction solution is refluxed until the reaction is completed. After being added into cooled ammonium chloride solution, it is extracted with ethyl acetate. The organic phase is concentrated by evaporation under vacuum, the residue is taken up in 5 ml of methanol and mixed with 0.5 ml of dilute hydrochloric acid (1/1). Ethyl acetate is added to the reaction solution, the organic phase is washed with sodium bicarbonate solution and concentrated by evaporation under vacuum. The crude product that is obtanied is purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 2/1).

Workup

  1. additionis added to the reaction solution
  2. temperatureThe reaction solution is refluxed until the reaction
  3. additionAfter being added
  4. extractionis extracted with ethyl acetate
  5. concentrationThe organic phase is concentrated by evaporation under vacuum
  6. additionmixed with 0.5 ml of dilute hydrochloric acid (1/1)
  7. additionEthyl acetate is added to the reaction solution
  8. washthe organic phase is washed with sodium bicarbonate solution
  9. concentrationconcentrated by evaporation under vacuum
  10. customThe crude product that is obtanied is purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 2/1)

Sources & evidence

ORD record
ord-47567398990e4a0cbb0405b4b15c7f25
Source dataset
uspto-grants-2008_08
Patent number
US07414043B2

Reaction notes

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