HCID 21261661, compound → HCID 21261646, compound

HRID 635001Notes

Reaction equation

HRID 635001 reaction equation
Br[C:2](Br)=[CH:3][CH2:4][C:5]([CH3:18])([CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.C([Li])CCC>O1CCCC1>[CH3:17][C:5]([CH3:18])([CH2:4][C:3]#[CH:2])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

Participants

4

Reactant 2

HCID 21261661HCID 21261661, compoundHCID 178418339Butyllithium

Product 1

HCID 21261646HCID 21261646, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.04 g of 2-(8,8-Dibromo-5,5-dimethyl-oct-7-enyloxy)-tetrahydro-pyrane (example1/step i]) (12.66 mmol) was dissolved in 55 ml of abs. tetrahydrofuran and treated at −78° with 25.3 ml of n-butyllithium (1.5 M, hexane, 3 eq.). 30 Min. later, the reaction mixture was poured onto crushed ice/NH4Cl, extracted twice with ether, washed with brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=95/5) gave 3.07 g of 2-(5,5-dimethyl-oct-7-ynyloxy)-tetrahydro-pyrane which was deprotected as follows: 2.00 g thereof (8.39 mmol) was dissolved in 57 ml of methanol, treated with 211 mg of pyridinium-(toluene-4-sulfonate) (0.1 eq.), and kept at room temperature for 1 night. The reaction mixture was then poured onto crushed ice/Na2CO3, extracted twice with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, pentane/methylacetate=75/25) gave 1.27 g of the title compound as colourless oil, 99% pure according to GC.

Workup

  1. additionlater, the reaction mixture was poured
  2. extractionextracted twice with ether
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-133b1a1ccc5045d8a5794a35ef65d825
Source dataset
uspto-grants-2001_02
Patent number
US06184422B2

Reaction notes

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