Tetrahydrofuran → 1(3H)-Isobenzofuranone,hexahydro-

HRID 1638400Notes

Reaction equation

HRID 1638400 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C(N([CH2:12][CH3:13])CC)C.O1C[CH2:17][CH2:16][CH2:15]1>>[C:2]1(=[O:3])[CH:13]2[CH:6]([CH2:15][CH2:16][CH2:17][CH2:12]2)[CH2:5][O:4]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 3446531(3H)-Isobenzofuranone,hexahydro-

Conditions

Temperature
12 °C

Procedure

At -5° C. and over a few minutes, a solution of 256 mg of ethyl chloroformate in 0.6 ml of tetrahydrofuran was added to a solution of 440 mg of the product of Step B'2 and 239 mg of triethylamine in 3.3 ml of tetrahydrofuran. The mixture was stirred for 30 minutes and then the precipitate was filtered off. The filtrate was added dropwise to a suspension of 235 mg of 95% sodium borohydride in 2.3 ml of water maintained at about 12° C. which was then left for 3 hours 30 minutes at ambient temperature. It was then cooled, acidified with 2N hydrochloric acid and extracted with methylene chloride. The extracts were dried, evaporated to dryness, purified by chromatography over silica (eluent: cyclohexane ethyl acetate, 65-35) to obtain 228 mg of (3a S, cis) hexahydro 1-(3H)-isobenzofuranone with a specific rotation of [α]D20 =-47° (c=0.6% in chloroform).

Workup

  1. waitAt -5° C. and over a few minutes
  2. filtrationthe precipitate was filtered off
  3. additionThe filtrate was added dropwise to a suspension of 235 mg of 95% sodium borohydride in 2.3 ml of water
  4. waitwas then left for 3 hours 30 minutes at ambient temperature
  5. temperatureIt was then cooled
  6. extractionextracted with methylene chloride
  7. customThe extracts were dried
  8. customevaporated to dryness
  9. custompurified by chromatography over silica (eluent: cyclohexane ethyl acetate, 65-35)

Sources & evidence

ORD record
ord-9d7c8ed9eeb244b7a6f8d9e8a33c55f0
Source dataset
uspto-grants-1989_11
Patent number
US04879392

Reaction notes

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