Tetrahydrofuran → trans-3-[3-(1-Dodecynyl)phenyl]propen-1-ol

HRID 1079071Notes

Reaction equation

[C:1]([C:13]1[CH:14]=[C:15](/[CH:19]=[CH:20]/[C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>C(OCC)(=O)C>[C:1]([C:13]1[CH:14]=[C:15]([CH2:19]/[CH:20]=[CH:21]/[OH:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of ethyl trans-3-[3-(1-dodecynyl)phenyl]-2-propenoate (10.0 g) and dry tetrahydrofuran (100 ml) at -78° C. was added diisobutylaluminum hydride (1.5M in toluene) (49 ml) slowly. The reaction mixture was stirred for 20 mins at -78° C., and 25% sodium hydroxide solution (3 ml) was added. The mixture was slowly warmed to room temperature and an additional 25% sodium hydroxide solution (3 ml) was added. The mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with ethyl acetate/hexane/1:3). The appropriate fractions were collected and evaporated to afford 7.14 g (81%) of product.

Workup

temperatureThe mixture was slowly warmed to room temperature
washwashed with water and brine
customThe organic phase was separated
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated in vacuo
customchromatographed over silica gel (eluted with ethyl acetate/hexane/1:3)
customThe appropriate fractions were collected
customevaporated

Sources & evidence

ORD record: ord-3ff7827ccc724faf95aba26fb8e89d3b
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05550247

Reaction notes

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