Tetrahydrofuran → Allyl 4-[alpha-methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoate

HRID 726468Notes

Reaction equation

HRID 726468 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:4][CH:3]=1.C1COCC1.C(N(CC)CC)C.[CH3:26][O:27][C:28]([CH:30]([C:34]1[CH:43]=[CH:42][C:41]2[C:40]([CH3:45])([CH3:44])[CH2:39][CH2:38][C:37]([CH3:47])([CH3:46])[C:36]=2[CH:35]=1)[C:31](Cl)=[O:32])=[O:29]>O>[CH3:26][O:27][C:28]([CH:30]([C:34]1[CH:43]=[CH:42][C:41]2[C:40]([CH3:45])([CH3:44])[CH2:39][CH2:38][C:37]([CH3:47])([CH3:46])[C:36]=2[CH:35]=1)[C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:12][CH:13]=1)=[O:32])=[O:29]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 53969402alpha-Methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetic acid chloride

Product 1

HCID 70275216Allyl 4-[alpha-methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetamido]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.8 g (10 mmol) of allyl 4-aminobenzoate, 50 ml of THF and 1.7 ml (12 mmol) of triethylamine were introduced into a round-bottomed flask. A solution of 3.3 g (10 mmol) of α-methoxycarbonyl-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acetic acid chloride in 25 ml of THP was added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction medium was poured into water, and extracted with ethyl acetate. The organic phase was decanted off, dried over magnesium sulfate and evaporated. The residue obtained was recrystallized from ethanol; 3.3 g (69%) of the expected compound of melting point 155°-156° C. were recovered after filtration and drying.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was decanted off
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas recrystallized from ethanol
  7. custom3.3 g (69%) of the expected compound of melting point 155°-156° C. were recovered
  8. filtrationafter filtration
  9. customdrying

Sources & evidence

ORD record
ord-cd1096d93f37428c9a062b69e3acbaae
Source dataset
uspto-grants-1998_01
Patent number
US05709867

Reaction notes

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