Chloroform → HCID 11067787, compound

HRID 2072344Notes

Reaction equation

HRID 2072344 reaction equation
[H-].COCCO[Al+]OCCOC.[Na+].[H-].C[O:16][C:17](=O)[CH2:18][C@:19]1([CH3:40])[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([CH3:39])[C:23]([CH3:38])=[C:24]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:25]=2[CH3:29])[O:20]1.[OH-].[Na+].C(Cl)(Cl)Cl>C1C=CC=CC=1>[CH2:31]([O:30][C:24]1[C:25]([CH3:29])=[C:26]2[C:21](=[C:22]([CH3:39])[C:23]=1[CH3:38])[O:20][C@:19]([CH3:40])([CH2:18][CH2:17][OH:16])[CH2:28][CH2:27]2)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 10948608(S)-(-)-methyl-6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-acetateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 11067787HCID 11067787, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A 70% solution of sodium bis (2-methoxyethoxy)-aluminum hydride in benzene (35 ml.) was stirred with ice bath cooling while a solution of 20.55 g. (0.0558 mole) of (S)-(-)-methyl-6-benzyloxy-2,5,7,8-tetramethyl- chroman-2-acetate in 50 ml. of benzene was added dropwise over 80 minutes keeping the temperature below 20° C. The resulting solution was stirred at room temperature for 2 hours then cautiously poured onto a mixture of ice and 1 N aqueous NaOH. Work-up by means of ether extraction in the manner of Example 1 afforded 19.8 g. of viscous colorless oil. This material was triturated with petroleum ether (30°-60° C.) and the resulting solid was filtered, washed with petroleum ether and dried under high vacuum giving 14.95 g. (78.7%) of (S)-(-)-6-benzylosy-2,5,7,8-tetramethyl-chroman-2-ethanol as a colorless solid, m.p. 55°-56° C.; [α]25D - 16.21° (c 2.03, CHCl3).

Workup

  1. temperaturecooling while a solution of 20.55 g
  2. customthe temperature below 20° C
  3. extractionWork-up by means of ether extraction in the manner of Example 1
  4. customafforded 19.8 g
  5. customThis material was triturated with petroleum ether (30°-60° C.)
  6. filtrationthe resulting solid was filtered
  7. washwashed with petroleum ether
  8. customdried under high vacuum
  9. customgiving 14.95 g

Sources & evidence

ORD record
ord-e16e40617daf4a0fb7603bdf9acd0b4b
Source dataset
uspto-grants-1977_09
Patent number
US04051153

Reaction notes

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