Methyl propiolate → Methyl 4-hydroxy-4-(5-indanyl)-2-butynoate

HRID 1651807Notes

Reaction equation

HRID 1651807 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][CH2:18][CH2:17]2)=[O:13].[Cl-].[NH4+]>O1CCCC1>[OH:13][CH:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[CH2:19][CH2:18][CH2:17]2)[C:3]#[C:2][C:1]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 13536Methyl propiolateHCID 25517Ammonium ChlorideHCID 1216245-IndanecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 23050455Methyl 4-hydroxy-4-(5-indanyl)-2-butynoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.8 ml (32 mmol) of methyl propiolate in 60 ml of tetrahydrofuran was treated at -78° under argon with 20 ml of n-butyllithium (1.6M in hexane). The mixture was stirred at -78° for 10 minutes and then a solution of 4.7 g (32 mmol) of 5-formylindane in 80 ml of tetrahydrofuran was added within 15 minutes. The reaction mixture was stirred at -78° for a further 10 minutes, then brought to room temperature and treated with 60 ml of saturated ammonium chloride solution. The aqeuous phase was extracted twice with ether. The combined organic phases were washed in succession with saturated sodium chloride solution and with water, dried over sodium sulphate and concentrated. The residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained methyl 4-hydroxy-4-(5-indanyl)-2-butynoate as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for a further 10 minutes
  2. custombrought to room temperature
  3. extractionThe aqeuous phase was extracted twice with ether
  4. washThe combined organic phases were washed in succession with saturated sodium chloride solution and with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on 500 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-b7665efd5740475d93420502f69fd9c3
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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