Tetrahydrofuran → HCID 59608898, compound

HRID 1047472Notes

Reaction equation

HRID 1047472 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH:10]([CH3:16])[CH:11]2[O:14][CH3:15])=[C:7]([CH2:17][CH2:18]O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C1C(=O)N([Br:51])C(=O)C1>>[Br:51][CH2:18][CH2:17][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]([CH3:16])[CH:11]2[O:14][CH3:15]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 59608934HCID 59608934, compound

Product 1

HCID 59608898HCID 59608898, compound

Conditions

Temperature
0 °C

Procedure

To a mixture of 27.58 g (105 mmol) of 2-(6-tert-butyl-1-methoxy-2-methyl-2,3-dihydro-1H-inden-4-yl)ethanol and 27.58 g (105 mmol) PPh3 in 450 ml of THF 18.72 g (105 mmol) of NBS was added at vigorous stirring for 5 min at 0° C. This mixture was stirred for 2 h at room temperature and then evaporated to dryness. A solution of the residue in 500 ml of hexanes was filtered through glass frit (G3), and the precipitate was additionally washed by 3×300 ml hexanes. The combined organic extract was evaporated to dryness. The product was isolated from the residue using flash chromatography on Silica Gel 60 (40-63 um, d 80 mm, 1250 mm; eluent: hexanes/ether=20/1, vol.). Yield 25.48 g (74%) of ca. 1 to 2 mixture of diastereomers.

Workup

  1. additionwas added
  2. stirringThis mixture was stirred for 2 h at room temperature
  3. customevaporated to dryness
  4. filtrationA solution of the residue in 500 ml of hexanes was filtered through glass frit (G3)
  5. washthe precipitate was additionally washed by 3×300 ml hexanes
  6. extractionThe combined organic extract
  7. customwas evaporated to dryness
  8. customThe product was isolated from the residue
  9. additionYield 25.48 g (74%) of ca. 1 to 2 mixture of diastereomers

Sources & evidence

ORD record
ord-da9001ee299b4e42b88ad47b8ec36e73
Source dataset
uspto-grants-2013_10
Patent number
US08569532B2

Reaction notes

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