Phosphoric Acid → HCID 15567161, compound

Isobutylene (7 ml) was condensed from a cylinder below -20° under N2 and diluted with precooled 25 ml CH2Cl2. This solution was cooled to -60° and there was added 2.9 g (21 mmol) of (3S,4S)-4-fluoro-1-octyne-3-ol, in 15 ml of CH2Cl2, 0.70 ml of BF3 etherate and 0.34 ml of anhydrous H3PO4, in the order given. The mixture was allowed to warm to 0°-15° and stirred for 40 min at that temperature. The resulting pale yellow solution was cooled again to -50° and poured into a vigorously stirred solution of saturated sodium bicarbonate (70 ml) kept cool in an ice water bath. The heterogeneous mixture was agitated vigorously until the organic layer became basic towards pH paper. The CH2Cl2 layer was separated, washed with water (40 ml ) and brine (30 ml) and dried over anhydrous Na2SO4. Concentration on a rotary evaporator afforded 9.87 g of a colorless oil which was chromatographed on 70 g of silica gel. Less polar impurities were eluted with hexane. Elution with pentane-ether 9:1 (100 ml) gave the crude t-butyloxy fluorooctyne, which on distillation under vacuum (bp 57° at 3-4 min) gave 3.69 g (91%) of pure material.

1. customcondensed from a cylinder below -20° under N2
2. temperatureThis solution was cooled to -60°
3. temperatureto warm to 0°-15°
4. temperatureThe resulting pale yellow solution was cooled again to -50°
5. temperaturekept cool in an ice water bath
6. stirringThe heterogeneous mixture was agitated vigorously until the organic layer
7. customThe CH2Cl2 layer was separated
8. washwashed with water (40 ml ) and brine (30 ml)
9. dry with materialdried over anhydrous Na2SO4
10. concentrationConcentration
11. customon a rotary evaporator

ORD record

ord-8b8220125ca24653b063120eda9c1cf5

Source dataset

uspto-grants-1982_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04309351