Hydrochloric Acid → HCID 86753103, compound

HRID 2393573Notes

Reaction equation

HRID 2393573 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].[BH4-].[Na+].Cl>C(Cl)Cl.CO>[C:1]([O:9][CH:10]1[CH2:18][CH:13]2[O:14][C:15](=[O:17])[CH2:16][CH:12]2[CH:11]1/[CH:19]=[CH:20]/[C@@H:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[OH:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 12070862HCID 12070862, compoundHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 86753103HCID 86753103, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of enone 4 (150 g, 392 mmol), cerium trichloride heptahydrate (152 g, 408 mmol), methanol (500 mL), and CH2Cl2 (1.5 L) at 0° C. was added NaBH4 (14.4 g) in 0.2 g portions over 1 h. After stirring for 2 h, the reaction was poured into 1M HCl (500 mL), the layers were separated, the aqueous layer was extracted with CH2 Cl2 (2×300 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated to provide 150.4 g (100%) of a 1:1 mixture of the two diastereomeric allylic alcohols. Separation of 200 g of the mixture (from several combined reactions) by HPLC (40% ethyl acetate in hexane) afforded 23.7 g (12%) of alcohol 42.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with CH2 Cl2 (2×300 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide
  7. customSeparation of 200 g of the mixture (from several combined reactions) by HPLC (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-928232f8e33b40f3993783c697c855a1
Source dataset
uspto-grants-1998_09
Patent number
US05807892

Reaction notes

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