HCID 11084950, compound → HCID 11413087, compound

HRID 538025Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][C@H:16]([OH:21])[CH2:17][C:18]#[C:19][CH3:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>COCCOC>[CH2:7]([O:14][CH2:15][C@H:16]([OH:21])[CH2:17]/[CH:18]=[CH:19]/[CH3:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Lithium aluminum hydride (93 g, 2.4 mol) was gradually added portion-wise to a 10-20° C. solution of C9 (167 g, 0.818 mol) in 1,2-dimethoxyethane (2.2 L), and the reaction was heated at 100° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, and was then quenched with ice followed by aqueous hydrochloric acid (2 M, 2 L) at 10-20° C. The resulting mixture was extracted with ethyl acetate (2 L), and the combined organic layers were dried over sodium sulfate and concentrated, affording the product as a pale brown oil. This material was used for the next step without further purification. Yield: 160 g, 0.78 mol, 95%. 1H NMR (400 MHz, CDCl3) δ 7.27-7.41 (m, 5H), 5.49-5.60 (m, 1H), 5.39-5.49 (m, 1H), 4.56 (s, 2H), 3.80-3.88 (m, 1H), 3.51 (dd, half of ABX pattern, J=9.5, 3.4 Hz, 1H), 3.39 (dd, half of ABX pattern, J=9.3, 1.9 Hz, 1H), 2.4 (br s, 1H), 2.16-2.24 (m, 2H), 1.66-1.70 (m, 3H).

Workup

customto a 10-20° C.
temperatureto cool to room temperature
customwas then quenched with ice
customfollowed by aqueous hydrochloric acid (2 M, 2 L) at 10-20° C
extractionThe resulting mixture was extracted with ethyl acetate (2 L)
dry with materialthe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-ab4bac2832074acf8077838e6eba036e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865706B2

Reaction notes

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