Ethyl bromoacetate → Ethyl-1-allyl-7-benzyloxy-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

HRID 224964Notes

Reaction equation

HRID 224964 reaction equation
[CH2:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[CH2:7][CH2:6][C:5]1=[O:22])[CH:2]=[CH2:3].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)(Cl)Cl>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][C:4]1([CH2:1][CH:2]=[CH2:3])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=2)[CH2:7][CH2:6][C:5]1=[O:22])[CH3:29]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 233307741-allyl-7-benzyloxy-3,4-dihydro-2(1H)-naphthalenone

Product 1

HCID 54132972Ethyl-1-allyl-7-benzyloxy-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Crude 1-allyl-7-benzyloxy-3,4-dihydro-2(1H)-naphthalenone (VIIIc), 22.9 g (78.5 mmol) was reacted with ethyl bromoacetate by the method of Example 5 to yield 25.5 g (87%) crude crystalline IXc. Recrystallization from ethanol gave 19.5 g (66%) m.p. 83°-85°. IR (CHCl3) 1725, 1710 cm-1 (ketone and ester); NMR δ, 1.05 and 3.96 (triplet and quartet for OCH2CH3) 4.8-5.8 (m, 5, olefinic and PhCH2O), 5.15 (s, 2, PhCH2O), 6.80-7.55 (m, 8, ArH).

Workup

  1. customto yield 25.5 g (87%) crude crystalline IXc
  2. customRecrystallization from ethanol
  3. customgave 19.5 g (66%) m.p. 83°-85°

Sources & evidence

ORD record
ord-d0e0ab1f242540a48023ada46f269add
Source dataset
uspto-grants-1980_11
Patent number
US04234731

Reaction notes

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