Lithium diisopropylamide → ethyl (E)-3-(3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enoate

HRID 1744912Notes

Reaction equation

HRID 1744912 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH2:24]([O:27][C:28]1[C:29]([C:42](=O)[CH2:43][CH3:44])=[CH:30][C:31]2[C:32]([CH3:41])([CH3:40])[CH2:33][CH2:34][C:35]([CH3:39])([CH3:38])[C:36]=2[CH:37]=1)[CH2:25][CH3:26]>C1COCC1>[CH2:24]([O:27][C:28]1[C:29](/[C:42](/[CH2:43][CH3:44])=[C:6](/[F:7])\[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:30][C:31]2[C:32]([CH3:41])([CH3:40])[CH2:33][CH2:34][C:35]([CH3:39])([CH3:38])[C:36]=2[CH:37]=1)[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22226103HCID 22226103, compound2×

Product 1

HCID 86593752ethyl (E)-3-(3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Triethyl 2-fluoro-2-phosphonoacetate (5.72 mL, 28.1 mmol, was added to a stirring solution of lithium diisopropylamide (28.1 mmol) in THF (54 mL) at −78° C. under argon. The dry ice bath was removed for about ten minutes, and then the solution was cooled again to −78° C. A solution of 1-(3-n-propoxy5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one (Intermediate 7, 2.70 g, 9.36 mmol) and THF. (10 mL) was added, and the solution was stirred at 0° C. for 2 h. The reaction was quenched at −78° C. by adding saturated ammonium chloride. The solution was warmed to room temperature and the products were extracted three times with ether. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound.

Workup

  1. customThe dry ice bath was removed for about ten minutes
  2. addition(10 mL) was added
  3. customThe reaction was quenched at −78° C.
  4. additionby adding saturated ammonium chloride
  5. temperatureThe solution was warmed to room temperature
  6. extractionthe products were extracted three times with ether
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a6917a40fd254206a8bde9b2a862d313
Source dataset
uspto-grants-2006_03
Patent number
US07019034B2

Reaction notes

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