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

HRID 1601171Notes

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 (1.5 M 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-d1675235ad1f4164939ca8a14e897d3d
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977147

Reaction notes

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