Oxirane, ((phenylmethoxy)methyl)-, (S)- (9CI) → HCID 11117222, compound

Temperature

0 °C

To a solution of (2S)-2-[(benzyloxy)methyl]oxirane (50 g, 305 mmol) in THF (1500 mL) at 0° C. was added copper bromide (4.37 g, 30.5 mmol). The resulting solution was stirred at 0° C. for 10 minutes and allylmagnesium bromide (1M in THF, 335 mL, 335 mmol) was added. The reaction was stirred for 2 hours at 0° C. and then quenched at 0° C. with saturated aqueous NH4Cl and diluted with DCM. The mixture was stirred at ambient temperature for 20 minutes and filtered to remove insoluble material. The filtrate was extracted with DCM (3×) and the combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. Flash column chromatography eluted with 10 to 40% EtOAc/hexanes provided (2S)-1-(benzyloxy)hex-5-en-2-ol. 1H NMR (400 MHz, CDCl2): δ 7.37-7.26 (m, 5 H); 5.88-5.74 (m, 1 H); 5.08-4.93 (m, 2 H); 4.54 (s, 2 H); 3.83 (s, 2 H); 3.53-3.44 (m, 1 H); 3.33 (dd, J=9.1, 8.2 Hz, 1 H); 2.49 (s, 1 H); 2.30-2.00 (m, 2 H); 1.64-1.39 (m, 2 H).

1. stirringThe reaction was stirred for 2 hours at 0° C.
2. customquenched at 0° C. with saturated aqueous NH4Cl
3. additiondiluted with DCM
4. stirringThe mixture was stirred at ambient temperature for 20 minutes
5. filtrationfiltered
6. customto remove insoluble material
7. extractionThe filtrate was extracted with DCM (3×)
8. dry with materialthe combined organic phases were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. washFlash column chromatography eluted with 10 to 40% EtOAc/hexanes

ORD record

ord-20eca2cdce7344f7a86dacd53b2656e3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513234B2