Tetrahydrofuran → (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one

HRID 277491Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C@@H:12]([OH:23])[CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C1COCC1.CCN(CC)CC>CCOC(C)=O.CCCCCC.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 40 °C

Procedure

A 100 mL three-necked flask was charged with (S)-3-(1,3-benzodioxol-5-yl)-6-propoxy-1H-inden-1-ol (1.9 g, 6.13 mmol), anhydrous THF (40 mL), Et3N (2.0 mL, 14.4 mmol) and Pd(dppe)Cl2 (130 mg, 0.227 mmol) under nitrogen. The mixture was warmed to 40° C. and after 6 h, cooled to room temperature, diluted with EtOAc/hexane solution (1:3, 60 mL) and filtered through SiO2. The filtrate was concentrated in vacuo affording (S)-3-(1,3-Benzodioxol-5-yl)-2,3-dihydro-6-propoxy-1H-inden-1-one as a yellow solid (1.85 g, 95%, 94% e.e.); mp 63.0-65.0 ° C.; Chiralpak AD column (93:7 IPA/hexane, 1 mL/min, 254 nm): 14.107 min (90.11%), 15.805 min (2.90%).1H NMR δ7.25-7.1 (m, 3H), 6.75 (d, J=7.9 Hz, 1H), 6.6 (dd, J=1.7, 8.0 Hz, 1H), 6.5 (d, J=1.7 Hz, 1H), 5.9 (s, 2H), 4.4 (dd,J=3.5, 7.8 Hz, 1H), 3.95 (t, J=6.5 Hz, 2H), 3.2 (dd, J=7.8, 19.3 Hz, 1H), 2.6 (dd, J=3.5, 19.1 Hz, 1H), 1.8 (quintet, J=7.8 Hz, 2H), 1.01 (t, J=7.4 Hz, 3H).

Workup

temperaturecooled to room temperature
filtrationfiltered through SiO2
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-e1c095b2d7444148bcfa4274a533f043
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355813B1

Reaction notes

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