HCID 54174194, compound → HCID 22914080, compound

HRID 1377442Notes

Reaction equation

HRID 1377442 reaction equation
[CH3:1][C:2]([CH:9]1[C:14]([CH3:16])([CH3:15])[CH:13]2[CH2:17][CH:10]1[CH2:11][CH2:12]2)([CH2:5][C:6]([CH3:8])=[CH2:7])[CH2:3][OH:4]>CCCCCCC>[CH3:7][C:6]1([CH3:8])[CH2:5][C:2]([CH3:1])([CH:9]2[C:14]([CH3:16])([CH3:15])[CH:13]3[CH2:17][CH:10]2[CH2:11][CH2:12]3)[CH2:3][O:4]1

Participants

3

Reactant 1

HCID 54174194HCID 54174194, compound

Product 1

HCID 22914080HCID 22914080, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

Similar to Example 4, 33.4 g of the alcohol from Example 52 at a purity of 96.8% (0.136 mole), 0.5 g of Amberlyst-15 and 150 ml of heptane were refluxed for 12 hours. After the usual work-up, 35.6 g of crude tetrahydrofuran was distilled to afford 31.8 g of purified product (98% yield). BP 75° C./0.08 mmHg; 1H-NMR (300 MHz), δ 1.01 (3H, s), 1.05 (3H, s), 1.21 (3H, s), 1.24 (3H, s), 1.31 (3H, s), 1.1-1.3 (2H, m), 1.35-2.05 (9H, m), 3.58 (2H, m); 13C-NMR (75 MHz), δ 23.67, 26.36, 26.63, 28.04, 29.24, 29.41, 32.22, 37.19, 41.65, 43.64, 48.23, 50.08, 58.60, 63.23, 77.49, 80.10; IR (Neat), 2980, 1460, 1370, 1060 cm-1 ; MS (m/e), 236 (M+), 221, 205, 193, 163, 149, 135, 125, 109, 43 (Base);

Workup

  1. distillationAfter the usual work-up, 35.6 g of crude tetrahydrofuran was distilled

Sources & evidence

ORD record
ord-144e223cf9644db9838babc55acbe98a
Source dataset
uspto-grants-1997_09
Patent number
US05665696

Reaction notes

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