Tetrahydrofuran → HCID 54413351, compound

HRID 1503190Notes

Reaction equation

HRID 1503190 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CC(P(OC)(O)=O)(C([O-])=[O:15])C.[C:22]([C:25]1C=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=2)[CH:26]=1)(=O)[CH3:23].[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>[NH4+].[Cl-]>[CH3:36][O:35][C:30](=[O:15])[CH:31]=[C:32]([C:27]1[CH:28]=[CH:29][C:38]2[C:25](=[CH:22][CH:23]=[C:41]([O:40][CH3:39])[CH:37]=2)[CH:26]=1)[CH3:33]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 775062-Acetyl-6-methoxynaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 53413272Trimethylphosphonoacetate

Product 1

HCID 54413351HCID 54413351, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a chilled (0° C.) solution of lithium bis(trimethylsilyl)amide (1.0 M, 50 mL) was dropwise added a solution of trimethylphosphonoacetate, keeping the temperature below 10° C. The solution was then allowed to warm to room temperature and stirred for an additional ten minutes after which a solution of 2-acetyl-6-methoxynaphthalene in THF (20 mL) was added in one portion. The solution was slowly heated to 50° C. for fourteen hours. The solution was cooled to room temperature then diluted with a 10% NH4Cl solution (100 mL), and extracted with ethyl acetate (2×100 mL). The organic layers were combined and dried over MgSO4, filtered, and filtrate concentrated to a white solid which was recrystallized from hexane/ethyl acetate to give 5.88 grams of 3-(6-methoxynaphthalen-2-yl)but-2-enoic acid methyl ester intermediate (92% yield).

Workup

  1. customthe temperature below 10° C
  2. additionwas added in one portion
  3. temperatureThe solution was slowly heated to 50° C. for fourteen hours
  4. temperatureThe solution was cooled to room temperature
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationfiltrate concentrated to a white solid which
  9. customwas recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-fdb42b4c00814851a136b85a6119d3ca
Source dataset
uspto-grants-2015_12
Patent number
US09212155B2

Reaction notes

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