Hydrochloric Acid → HCID 56636518, compound

HRID 638627Notes

Reaction equation

HRID 638627 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[C@H:14]([CH2:15][CH2:16]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:13][CH2:12][C@H:11]1[O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:35]([Mg]Br)[CH3:36].[Cl-].[Li+].Cl>O1CCCC1.C(OCC)C>[CH2:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15][CH2:16][CH2:35][CH3:36])[CH2:13][CH2:12][C@H:11]1[O:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][O:30]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 18601028HCID 18601028, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 56636518HCID 56636518, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a flow of argon, to a solution cooled to -78° C., of 13.6 g of (1R,2S,3S)-2-benzyloxymethyl-1-(2-tetrahydropyranyloxy)-3-[2-(p-toluenesulphonyloxy)ethyl]cyclopentane (prepared in Reference Example 5) in 30 ml of dry tetrahydrofuran, 12.5 ml of a 3M solution of ethyl magnesium bromide in diethyl ether was added over a period of 10 min; to the solution, 5 ml of a solution of 8.4 g of lithium chloride and 13.4 g of cupric chloride in 1 l of tetrahydrofuran was added dropwise over a period of 5 min. The mixture was stirred further for 1.5 hrs at the same temperature, for 2 hrs at 0° C., and for 16 hrs at room temperature. The reaction solution was poured into a mixture of 70 ml of 1N hydrochloric acid, ice and 150 ml of diethyl ether, and the ether layer separated was washed with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (5:1) as eluent to give 8.63 g of the title compound having the following physical characteristics, in a 89.8% yield.

Workup

  1. additionwas added over a period of 10 min
  2. waitfor 16 hrs at room temperature
  3. customthe ether layer separated
  4. washwas washed with an aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (5:1) as eluent

Sources & evidence

ORD record
ord-303a342c7caa4db782fb915d411b6cd8
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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