Hydrochloric Acid → HCID 10381501, compound

HRID 2257248Notes

Reaction equation

HRID 2257248 reaction equation
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16](=[O:21])[CH:17]=[C:18]([CH3:20])[CH3:19])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[ClH:23]>>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:14])([CH3:15])[C:9]=2[CH:8]=[C:7]([C:16](=[O:21])[CH2:17][C:18]([Cl:23])([CH3:20])[CH3:19])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 10517348HCID 10517348, compound

Product 1

HCID 10381501HCID 10381501, compound

Procedure

A solution of 1-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-3-methyl-2-buten-1-one (Example 12) (2.0 g, 6.2 mmol) in HCl-saturated Et2O (30 mL) is stirred at 25° C. overnight. The solution is treated with H2O (20 mL), and partitioned against CH2Cl2 (3×20 mL). The combined organic layers are dried (MgSO4), filtered, and evaporated to a cream-colored solid which is crystallized from hexane to give 1-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-3-chloro-3-methylbutan-1-one.

Workup

  1. custompartitioned against CH2Cl2 (3×20 mL)
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to a cream-colored solid which
  5. customis crystallized from hexane

Sources & evidence

ORD record
ord-afe6f1908ad64bcd993dc1948c6a0537
Source dataset
uspto-grants-1997_08
Patent number
US05656661

Reaction notes

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