Methanol → HCID 9977855, compound

HRID 1784155Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:16]=[CH:15][C@H:14]([CH3:17])[C@H:13]([OH:18])[C@@H:12]([CH3:19])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.[Si:28](OS(C(F)(F)F)(=O)=O)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].CO>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:16]=[CH:15][C@H:14]([CH3:17])[C@H:13]([O:18][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C@@H:12]([CH3:19])[CH:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of alcohol 32 (550 mg, 1.98 mmol) and 2,6-lutidine (0.34 mL, 2.97 mmol) in CH2Cl2 (20 mL) was cooled to −78° C., and 0.55 mL (2.39 mmol) of TBSOTf was added. The cold solution was stirred and allowed to warm to 0° C. over a 1 h. MeOH (40 μL, 1 mmol) was then added and the resulting mixture was concentrated via rotary evaporation. The crude residue was purified with flash column chromatography (EtOAc/hexanes; 1:5) to afford 760 mg (98%) of 33 as colorless oil. [α]20D=+126.7 (c=0.80, CH2Cl2); 1H NMR (CDCl3, 300 MHz) δ 7.86-7.90 (m, 2H), 7.50-7.64 (m, 3H), 7.09 (d, J=5.4 Hz, 1H), 6.06 (dt, J=11.7 Hz, 1.5 Hz, 1H), 5.80 (dd, J=11.7 Hz, 5.1 Hz, 1H), 3.66 (dd, J=6.3 Hz, 2.1 Hz, 1H), 2.70 (m, 1H), 2.47 (m. 1H), 1.18 (d, J=7.2 Hz, 3H), 1.06 (d, J=7.2 Hz, 3H), 0.81 (s, 9H), 0.038 (s, 3H), 0.032 (s, 3H); 13C NMR (CDCl3, 75 MHz) δ 142.8, 140.4, 140.2, 137.8, 133.2, 129.3, 128.0, 118.4, 76.8, 41.4, 38.8, 26.0, 19.1, 18.2, 16.7, −4.1, −4.4; LRMS (CI): m/z 393 [M+H]+; HRMS (CI) calculated for C21H32O3SSi, 392.1841; found, 392.1840.

Workup

concentrationthe resulting mixture was concentrated via rotary evaporation
customThe crude residue was purified with flash column chromatography (EtOAc/hexanes; 1:5)

Sources & evidence

ORD record: ord-1c02daaec61d4b3cbef197317b0fd01b
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501535B2

Reaction notes

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