Hydrochloric Acid → HCID 21107272, compound

HRID 1765813Notes

Reaction equation

HRID 1765813 reaction equation
C([O:3][C:4](=[O:25])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:16]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].Cl>C(O)C.O1CCCC1>[C:21]([C:17]1[CH:16]=[C:15]([C:14]#[C:13][C:10]2[CH:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C:4]([OH:25])=[O:3])=[CH:8][CH:9]=2)[CH:20]=[CH:19][CH:18]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18965814HCID 18965814, compound2×

Product 1

HCID 21107272HCID 21107272, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-3-[4-(3-tert-butyl-phenylethynyl)-phenyl]-acrylic acid ethyl ester (Intermediate 103, 0.015 g, 0.047 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with a 2M solution of lithium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was neutralized with 10% aqueous hydrochloric acid and evaporated in vacuo to a solid that was washed with water and hexane and dried to afford the title product as a white solid (0.012 g, 85%). 1H NMR (300 MHz, CDCl3): δ 7.78 (d, 1H, J=16.2 Hz), 7.59–7.26 (m, 8H), 6.47 (d, 1H, J=16.2 Hz), 1.34 (s, 9H).

Workup

  1. customthe resulting reaction mixture
  2. customevaporated in vacuo to a solid
  3. washthat was washed with water and hexane
  4. customdried

Sources & evidence

ORD record
ord-0dfc9e9cde824e19b9935c23d555957a
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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