Hydrochloric Acid → HCID 15389073, compound

HRID 428216Notes

Reaction equation

HRID 428216 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C(OCC)(=O)C.O.CO>[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:25])([CH3:26])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 15389070HCID 15389070, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15389073HCID 15389073, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

760 mg (2.2 mmol) of methyl 2-hydroxy-4-[3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate and 20 ml of toluene are introduced into a three-necked flask under a stream of nitrogen. 4.4 ml of diisobutylaluminium hydride (1 M in toluene) are added at −78° C. and the mixture is allowed to return to room temperature. 9 ml of methanol and then 9 ml of hydrochloric acid (1 N) are successively introduced. The reaction medium is poured into an ethyl acetate/water mixture and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (50/50% by volume). After evaporation of the solvents, 200 mg (30%) of the expected alcohol are collected, with a melting point of 94-5° C.

Workup

  1. customto return to room temperature
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluted with a mixture of ethyl acetate and heptane (50/50% by volume)
  7. customAfter evaporation of the solvents, 200 mg (30%) of the expected alcohol
  8. customare collected, with a melting point of 94-5° C.

Sources & evidence

ORD record
ord-9b159121213a4cfb8a282d05267c64b7
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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