Hydrochloric Acid → HCID 19353119, compound

HRID 378219Notes

Reaction equation

HRID 378219 reaction equation
C[Li].[CH2:3]([O:5]CC)[CH3:4].[CH3:8][C:9]1([CH3:36])[CH2:18][CH2:17][C:16]([CH3:20])([CH3:19])[C:15]2[CH:14]=[C:13]([C:21]3([CH3:35])[C:25]4[CH:26]=[C:27](C=CC(O)=O)[CH:28]=[CH:29][C:24]=4[O:23][CH2:22]3)[CH:12]=[CH:11][C:10]1=2.Cl>C1COCC1>[CH3:35][C:21]1([C:13]2[CH:12]=[CH:11][C:10]3[C:9]([CH3:8])([CH3:36])[CH2:18][CH2:17][C:16]([CH3:19])([CH3:20])[C:15]=3[CH:14]=2)[C:25]2[CH:26]=[C:27]([C:3](=[O:5])[CH3:4])[CH:28]=[CH:29][C:24]=2[O:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 54110933HCID 54110933, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19353119HCID 19353119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A 1.6M methyllithium solution in ethyl ether (3.4 ml, 5.4 mmol) is added to a solution of 3-Methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2,3-dihydrobenzofuran-5-carboxylic acid (Example 2) (900 mg, 4.47 mmol) in THF (50 ml) at -20° C. The mixture is stirred for 4 h at -20° C. and is then poured onto ethyl acetate and a 1N hydrochloric acid solution. The organic phase is washed 2 times with water, dried over anhydrous magnesium sulphate and concentrated in vacuo at 40° C. in a rotary evaporator.

Workup

  1. additionis then poured onto ethyl acetate
  2. washThe organic phase is washed 2 times with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated in vacuo at 40° C. in a rotary evaporator

Sources & evidence

ORD record
ord-61c420c6b65445d6aa477feef5190e59
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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