Propanal → HCID 131731945, compound

HRID 536781Notes

Reaction equation

HRID 536781 reaction equation
[CH2:1]([C@H:8]1[C@H:12]([CH2:13][C:14]#[CH:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:18]([Li])[CH2:19][CH2:20]C.C(=[O:26])CC>C1COCC1>[CH2:1]([C@@H:8]1[O:9][C:10]([CH3:16])([CH3:17])[O:11][C@H:12]1[CH2:13][CH2:14][CH:15]([OH:26])[C:18]#[C:19][CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 527PropanalHCID 11020974HCID 11020974, compoundHCID 178418339Butyllithium

Product 1

HCID 131731945HCID 131731945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (4S,5S)-4-heptyl-2,2-dimethyl-5-(prop-2-ynyl)-1,3-dioxolane (19.4 mg, 0.081 mmol) in THF (0.8 mL) at −78° C. was added n-butyllithium (51 μL, 1.6 M). The mixture was stirred for 30 min. at which time propanal (excess) was added. The mixture was stirred at −78° C. for an additional 30 min. The reaction was quenched with sat'd NH4Cl (aq.) at −78° C. The title compound was isolated using a standard workup (22 mg, 92%). 1H NMR (400 MHz, CDCl3) δ 4.30 (m, 1H), 3.81 (dt, 4 Hz, 7.6 Hz, 1H), 3.71 (m, 1H), 2.54 (dd, 1.6 Hz, 5.2 Hz, 2H), 1.39 (s, 6H), 1.28 (m, 12H), 0.99 (t, 7.6 Hz, 3H), 0.87 (t, 6.4 Hz, 3H). LRMS (APCI+) found 279.7, [M−H2O]+.

Workup

  1. additionwas added
  2. customThe reaction was quenched with sat'd NH4Cl (aq.) at −78° C

Sources & evidence

ORD record
ord-9cb118ddc98c4311895cb06beaa00005
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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