Toluene → HCID 59070418, compound

HRID 2393572Notes

Reaction equation

HRID 2393572 reaction equation
[CH:1]1([C@H:7]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)/[CH:8]=[CH:9]/[C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]3)[CH2:12][C@H:11]2[O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[CH:1]1([C@H:7]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)/[CH:8]=[CH:9]/[C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][CH:15]([OH:18])[CH2:16]3)[CH2:12][C@H:11]2[O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 70388835HCID 70388835, compound

Product 1

HCID 59070418HCID 59070418, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lactone 24 (5.7 g, 12.7 mmol) in 40 mL of THF at -78° C. was added dropwise a 1.5M solution of DIBAL-H in toluene (11.5 mL, 17.2 mmol). After 2 h, the reaction was poured into 70 mL of a saturated solution of sodium potassium tartrate and was stirred for 30 min. The mixture was extracted with ethyl acetate (3×50 mL), the combined organic layers were dried over MgSO4, filtered and concentrated, and the residue was chromatographed on silica gel (1/1 hexane/ethyl acetate) to afford 4.7 g (82%) of lactol 35.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel (1/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-707021569b4c4928b4276d95673d2c94
Source dataset
uspto-grants-1998_09
Patent number
US05807892

Reaction notes

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