Lithium hydroxide, monohydrate → HCID 70416008, compound

HRID 569484Notes

Reaction equation

HRID 569484 reaction equation
[C:1]([C:9]1[O:13][C:12]([CH:14]=[C:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.[OH-].[Li+]>C1COCC1.O>[CH2:19]([O:18][C:16](=[O:17])/[C:15](=[CH:14]\[C:12]1[O:13][C:9]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1)/[C:21]([OH:23])=[O:22])[CH3:20]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 20147169HCID 20147169, compound

Product 1

HCID 70416008HCID 70416008, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

Diethyl 2-[5-(1-octynyl)-2-furanylmethylene]propan-1,3-dioate (1.04 g, 3 mmole from Example 10) was added to a solution of lithium hydroxide monohydrate (0.13 g, 1 eq) in THF/water (1:1, 15 ml) and the mixture was heated to 70° C. for 3 hr. The resulting clear solution was acidified and then extracted into diethyl ether (2×50 ml). The etheral solution was dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as a yellow solid which was recrystallised from hexane 0.65 g (68%), mp 89°-90° C., νmax (mull), 2600(broad), 2220, 1740, 1695, 1615, 1555, 1270, 1235, 1215 cm-1 ; δ(CDCl3), 0.89(3H, distorted t), 1.43(3H, t, J=7.5 Hz), 1.45(8H, m), 2.42 (2H, t, J=6.5 Hz), 4.40(2H, q, J=7.5 Hz), 6.54(1H, d, J=3.0 Hz), 6.86(1H, d, J=3.0 Hz), 7.57(1H, s), 11.5(1H, s).

Workup

  1. extractionextracted into diethyl ether (2×50 ml)
  2. dry with materialThe etheral solution was dried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d807184c9e004bfa8269cabe70dfd553
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Reaction notes

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