Ethanol → HCID 21314007, compound

HRID 971445Notes

Reaction equation

HRID 971445 reaction equation
O.O=C[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([CH:15]=1)[C:11]([O:13]C)=O)=[O:5].Cl.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([CH3:37])([NH2:36])[CH3:35])=[CH:28][CH:27]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[CH2:45](O)C>O1CCCC1>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][C:34]([NH:36][CH2:45][C:15]2[C:10]([CH2:11][OH:13])=[C:9]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:8]=[CH:7][C:6]=2[CH2:4][OH:5])([CH3:37])[CH3:35])=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 131711552HCID 131711552, compoundHCID 131711553HCID 131711553, compound

Product 1

HCID 21314007HCID 21314007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Crude 5-(oxoacetyl)-2-(phenylmethoxy)benzoic acid, methyl ester, hydrate (prepared in 15b above) in ethanol (100 ml) was treated with 4-(4-fluorophenyl)-2-methyl-2-butanamine (generated from its hydrochloride salt (1.5 g) prepared in (c) above). The solution was boiled for 30 min. and then evaporated to leave a yellow gum. The gum in dry tetrahydrofuran (50 ml) was dripped into a stirred solution of lithium aluminium hydride (1.0 g) in dry tetrahydrofuran (50 ml) at room temperature. The mixture was stirred for 20 hr. then boiled for 2 hr. Water (5 ml) was slowly added, the mixture was filtered and the filtrate was evaporated to leave a colourless gum which crystallised from ether-light petroleum (b.p. 60°-80°) as colourless needles, m.p. 76°-79° (0.37 g).

Workup

  1. customevaporated
  2. customto leave a yellow gum
  3. waitthen boiled for 2 hr
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated
  6. customto leave a colourless gum which
  7. customcrystallised from ether-light petroleum (b.p. 60°-80°) as colourless needles, m.p. 76°-79° (0.37 g)

Sources & evidence

ORD record
ord-7edcc9ecc6834fae9bddab7f1c42a764
Source dataset
uspto-grants-1979_07
Patent number
US04160036

Reaction notes

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