Methyl iodide → HCID 13671501, compound

HRID 868009Notes

Reaction equation

HRID 868009 reaction equation
Cl.N1(CCC2CCCC3C(C(O)=O)=CC=CC2=3)C=CN=C1.IC.[OH:24][CH2:25][CH2:26][C:27]1[C:28]2[CH:29]=[CH:30][C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][C:33]=2[CH2:34][CH2:35][CH:36]=1>C(O)C.[C].[Pd]>[OH:24][CH2:25][CH2:26][CH:27]1[CH2:36][CH2:35][CH2:34][C:33]2[CH:32]=[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:30]=[CH:29][C:28]1=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 13671507HCID 13671507, compoundHCID 21289511HCID 21289511, compound

Product 1

HCID 13671501HCID 13671501, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

14.3 g of the above product was allowed to react using procedures analogous to those described in steps (5) and (6) of Referential Example 1 but using iodomethane instead of bromoethane to give an oily product containing a small amount of ethyl 5-(2-hydroxyethyl)-7,8-dihydro-2-naphthalenecarboxylate as a by-product. The product was dissolved in 10 ml of ethanol and 0.5 g of 10% palladium carbon was added thereto. The mixture was catalytically reduced. After absorption of hydrogen gas was completed, the catalyst was removed by filtration. The filtrate was concentrated in vacuo to give 1.4 g of ethyl 5-(2-hydroxyethyl)-5,6,7,8-tetrahydro-2-naphthalenecarboxylate as an oil.

Workup

  1. customto react
  2. customto give an oily product
  3. customAfter absorption of hydrogen gas
  4. customthe catalyst was removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-249aae03ecc1488d888503999aa9ce18
Source dataset
uspto-grants-1988_10
Patent number
US04777257

Reaction notes

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