Diisobutylaluminum hydride → HCID 86736699, compound

HRID 1105764Notes

Reaction equation

HRID 1105764 reaction equation
[CH3:1][C@@H:2]1[O:8][C:7](=[O:9])[CH2:6][C@@H:5]2[C@H:3]1[O:4]2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[O:9]=[CH:7][CH2:6][C@H:5]1[O:4][C@H:3]1[C@H:2]([CH3:1])[OH:8]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 12817969HCID 12817969, compound

Product 1

HCID 86736699HCID 86736699, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 2.58 g (20 mmol) of (1S,2S,6R)-2-methyl-3,7-dioxabicyclo[4.1.0]-heptan-4-one in 300 ml of anhydrous toluene cooled to -75° was added under argon 14 ml (24.5 mmol) of a 1.75 M solution of DIBAL-H in toluene. The reaction mixture was stirred at -75° for 2 hr and then quickly poured onto a slurry of 260 g of silica gel (Silica Gel 60 Merck) in toluene and allowed to filter. The slurry was washed with 3 L of methylene chloride-methanol(9:1). The combined filtrate and washings were evaporated to dryness under reduced pressure. The residual oil was distilled with a Kugelrohr distillation apparatus to afford 3,4-anhydro-2,6-dideoxy-L-ribo-hexose: bp 90° (oven temperature) (0.1 mm); [α]25D +25.16° (c 1.013, MeOH).

Workup

  1. filtrationto filter
  2. washThe slurry was washed with 3 L of methylene chloride-methanol(9:1)
  3. customThe combined filtrate and washings were evaporated to dryness under reduced pressure
  4. distillationThe residual oil was distilled with a Kugelrohr distillation apparatus

Sources & evidence

ORD record
ord-78fc3b6ec9de4873964e9abe7c7f235e
Source dataset
uspto-grants-1982_01
Patent number
US04310462

Reaction notes

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