HCID 20058703, compound → HCID 53829528, compound

HRID 2050646Notes

Reaction equation

HRID 2050646 reaction equation
[CH3:1][Mg]Cl.[O:4]=[C:5]([CH3:32])[CH2:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>O1CCCC1>[OH:4][C:5]([CH3:1])([CH3:32])[CH2:6][CH:7]([C:20]1[CH:21]=[C:22]([Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])[O:23][CH:24]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 20058703HCID 20058703, compound2×HCID 178418332HCID 178418332, compound

Product 1

HCID 53829528HCID 53829528, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of methylmagnesium chloride (a 3 M solution in tetrahydrofuran; 0.68 ml, 2.04 mmol) and 4-[1-(2-oxopropyl)tridecyl]-2-tert-butyldimethylsilylfuran (Compound 31, 429 mg, 1.02 mmol) in tetrahydrofuran (3 ml) was stirred at 0° at room temperature for 6 hours. The mixture was quenched with saturated ammonium chloride and extracted with ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was chromatographed on a silica column using 5% ethyl acetate/hexane to give the title alcohol.

Workup

  1. customThe mixture was quenched with saturated ammonium chloride
  2. extractionextracted with ether
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customwas chromatographed on a silica column

Sources & evidence

ORD record
ord-93213348ead745c89bee3055efb64f4c
Source dataset
uspto-grants-1991_05
Patent number
US05013850

Reaction notes

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