Water → 2-(7-phenylhept-6-ynyloxy)tetrahydro-2H-pyrane

HRID 269424Notes

Reaction equation

HRID 269424 reaction equation
[Li]CCCC.[C:6]1([C:12]#[CH:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.O>O1CCCC1>[C:6]1([C:12]#[C:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10821PhenylacetyleneHCID 117021222-(5-Iodo-pentyloxy)-tetrahydro-pyranHCID 178418339Butyllithium2×

Product 1

HCID 589246782-(7-phenylhept-6-ynyloxy)tetrahydro-2H-pyrane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

BuLi (33.3 mL, 50 mmol, 1.5 M) was added in drops to a magnetically stirred solution of phenyl acetylene (5.11 g, 50 mmol) in dry tetrahydrofuran (200 mL) at 0° C. in a nitrogen atmosphere. After all the BuLi had been added, the reaction mixture was stirred at 0° C. for 30 minutes. A solution of 2-(5-iodpentyloxy)tetrahydro-2H-pyrane (9) (14.91 g, 50 mmol) in dry tetrahydrofuran (100 mL) was added in drops at 0° C. Adding completed, the reaction mixture was allowed to reach room temperature in order then to be refluxed over night. The reaction was monitored by thin-layer chromatography (TLC). When all the base material had been converted, water (300 mL) was added and the aqueous phase was extracted with petroleum ether (boiling point 40-60° C.) (6×50 mL). The combined organic phases were washed with water (4×25 mL) and dried (MgSO4). Petroleum ether was distilled out on a rotary evaporator, yielding 11.6 g (85%). NMR indicated a pure product, and further purification was therefore not necessary.

Workup

  1. additionAdding
  2. customto reach room temperature in order
  3. temperatureto be refluxed over night
  4. extractionthe aqueous phase was extracted with petroleum ether (boiling point 40-60° C.) (6×50 mL)
  5. washThe combined organic phases were washed with water (4×25 mL)
  6. dry with materialdried (MgSO4)
  7. distillationPetroleum ether was distilled out on a rotary evaporator
  8. customyielding 11.6 g (85%)
  9. customa pure product, and further purification

Sources & evidence

ORD record
ord-66818624583e488eaa70bfaa6558bbc9
Source dataset
uspto-grants-2008_11
Patent number
US07446226B2

Reaction notes

Loading…