Tetrahydrofuran → HCID 59608871, compound

HRID 1047475Notes

Reaction equation

[CH3:1][O:2][CH:3]1[C:11]2[C:6](=[C:7]([CH2:14][CH2:15]O)[C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=2)[CH2:5][CH:4]1[CH3:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C1C(=O)N([Br:49])C(=O)C1>>[Br:49][CH2:15][CH2:14][C:7]1[C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=[C:11]2[C:6]=1[CH2:5][CH:4]([CH3:17])[CH:3]2[O:2][CH3:1]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 11776Triphenylphosphine

HCID 67184N-bromobutanimide

HCID 59608877HCID 59608877, compound

Product 1

HCID 59608871HCID 59608871, compound

Conditions

Temperature: 0 °C

Procedure

To a mixture of 36.66 g (156.44 mmol) of 2-(1-methoxy-2,5,6-trimethyl-2,3-dihydro-1H-inden-4-yl)ethanol and 41 g (156.44 mmol) PPh3 in 650 ml of THF 27.85 g (156.44 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 31.38 g (67%) of ca. 1 to 2 mixture of diastereomers.

Workup

additionwas added
stirringThis mixture was stirred for 2 h at room temperature
customevaporated to dryness
filtrationA solution of the residue in 500 ml of hexanes was filtered through glass frit (G3)
washthe precipitate was additionally washed by 3×300 ml hexanes
extractionThe combined organic extract
customwas evaporated to dryness
customThe product was isolated from the residue
additionYield 31.38 g (67%) of ca. 1 to 2 mixture of diastereomers

Sources & evidence

ORD record: ord-e0858532845646ccbef8182db1bd613a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569532B2

Reaction notes

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